CINXE.COM

<!DOCTYPE html> <html class="client-nojs vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-sticky-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-1 vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day vector-toc-available" lang="en" dir="ltr"> <head> <meta charset="UTF-8"> <title>Larock indole synthesis - Wikipedia</title> <script>(function(){var className="client-js vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-sticky-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-1 vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day vector-toc-available";var cookie=document.cookie.match(/(?:^|; )enwikimwclientpreferences=([^;]+)/);if(cookie){cookie[1].split('%2C').forEach(function(pref){className=className.replace(new RegExp('(^| )'+pref.replace(/-clientpref-\w+$|[^\w-]+/g,'')+'-clientpref-\\w+( |$)'),'$1'+pref+'$2');});}document.documentElement.className=className;}());RLCONF={"wgBreakFrames":false,"wgSeparatorTransformTable":["",""],"wgDigitTransformTable":["",""],"wgDefaultDateFormat":"dmy", "wgMonthNames":["","January","February","March","April","May","June","July","August","September","October","November","December"],"wgRequestId":"8bdb4a33-2713-45ca-a8e7-b494710505fd","wgCanonicalNamespace":"","wgCanonicalSpecialPageName":false,"wgNamespaceNumber":0,"wgPageName":"Larock_indole_synthesis","wgTitle":"Larock indole synthesis","wgCurRevisionId":1173388557,"wgRevisionId":1173388557,"wgArticleId":2381942,"wgIsArticle":true,"wgIsRedirect":false,"wgAction":"view","wgUserName":null,"wgUserGroups":["*"],"wgCategories":["CS1 maint: multiple names: authors list","Articles with short description","Short description matches Wikidata","Ring forming reactions","Indole forming reactions","Name reactions"],"wgPageViewLanguage":"en","wgPageContentLanguage":"en","wgPageContentModel":"wikitext","wgRelevantPageName":"Larock_indole_synthesis","wgRelevantArticleId":2381942,"wgIsProbablyEditable":true,"wgRelevantPageIsProbablyEditable":true,"wgRestrictionEdit":[],"wgRestrictionMove":[], "wgNoticeProject":"wikipedia","wgCiteReferencePreviewsActive":false,"wgFlaggedRevsParams":{"tags":{"status":{"levels":1}}},"wgMediaViewerOnClick":true,"wgMediaViewerEnabledByDefault":true,"wgPopupsFlags":0,"wgVisualEditor":{"pageLanguageCode":"en","pageLanguageDir":"ltr","pageVariantFallbacks":"en"},"wgMFDisplayWikibaseDescriptions":{"search":true,"watchlist":true,"tagline":false,"nearby":true},"wgWMESchemaEditAttemptStepOversample":false,"wgWMEPageLength":10000,"wgRelatedArticlesCompat":[],"wgCentralAuthMobileDomain":false,"wgEditSubmitButtonLabelPublish":true,"wgULSPosition":"interlanguage","wgULSisCompactLinksEnabled":false,"wgVector2022LanguageInHeader":true,"wgULSisLanguageSelectorEmpty":false,"wgWikibaseItemId":"Q2783827","wgCheckUserClientHintsHeadersJsApi":["brands","architecture","bitness","fullVersionList","mobile","model","platform","platformVersion"],"GEHomepageSuggestedEditsEnableTopics":true,"wgGETopicsMatchModeEnabled":false, "wgGEStructuredTaskRejectionReasonTextInputEnabled":false,"wgGELevelingUpEnabledForUser":false};RLSTATE={"ext.globalCssJs.user.styles":"ready","site.styles":"ready","user.styles":"ready","ext.globalCssJs.user":"ready","user":"ready","user.options":"loading","ext.cite.styles":"ready","skins.vector.search.codex.styles":"ready","skins.vector.styles":"ready","skins.vector.icons":"ready","ext.wikimediamessages.styles":"ready","ext.visualEditor.desktopArticleTarget.noscript":"ready","ext.uls.interlanguage":"ready","wikibase.client.init":"ready","ext.wikimediaBadges":"ready"};RLPAGEMODULES=["ext.cite.ux-enhancements","mediawiki.page.media","site","mediawiki.page.ready","mediawiki.toc","skins.vector.js","ext.centralNotice.geoIP","ext.centralNotice.startUp","ext.gadget.ReferenceTooltips","ext.gadget.switcher","ext.urlShortener.toolbar","ext.centralauth.centralautologin","mmv.bootstrap","ext.popups","ext.visualEditor.desktopArticleTarget.init","ext.visualEditor.targetLoader", "ext.echo.centralauth","ext.eventLogging","ext.wikimediaEvents","ext.navigationTiming","ext.uls.interface","ext.cx.eventlogging.campaigns","ext.cx.uls.quick.actions","wikibase.client.vector-2022","ext.checkUser.clientHints","ext.growthExperiments.SuggestedEditSession","wikibase.sidebar.tracking"];</script> <script>(RLQ=window.RLQ||[]).push(function(){mw.loader.impl(function(){return["user.options@12s5i",function($,jQuery,require,module){mw.user.tokens.set({"patrolToken":"+\\","watchToken":"+\\","csrfToken":"+\\"}); }];});});</script> <link rel="stylesheet" href="/w/load.php?lang=en&modules=ext.cite.styles%7Cext.uls.interlanguage%7Cext.visualEditor.desktopArticleTarget.noscript%7Cext.wikimediaBadges%7Cext.wikimediamessages.styles%7Cskins.vector.icons%2Cstyles%7Cskins.vector.search.codex.styles%7Cwikibase.client.init&only=styles&skin=vector-2022"> <script async="" src="/w/load.php?lang=en&modules=startup&only=scripts&raw=1&skin=vector-2022"></script> <meta name="ResourceLoaderDynamicStyles" content=""> <link rel="stylesheet" href="/w/load.php?lang=en&modules=site.styles&only=styles&skin=vector-2022"> <meta name="generator" content="MediaWiki 1.44.0-wmf.4"> <meta name="referrer" content="origin"> <meta name="referrer" content="origin-when-cross-origin"> <meta name="robots" content="max-image-preview:standard"> <meta name="format-detection" content="telephone=no"> <meta name="viewport" content="width=1120"> <meta property="og:title" content="Larock indole synthesis - Wikipedia"> <meta property="og:type" content="website"> <link rel="preconnect" href="//upload.wikimedia.org"> <link rel="alternate" media="only screen and (max-width: 640px)" href="//en.m.wikipedia.org/wiki/Larock_indole_synthesis"> <link rel="alternate" type="application/x-wiki" title="Edit this page" href="/w/index.php?title=Larock_indole_synthesis&action=edit"> <link rel="apple-touch-icon" href="/static/apple-touch/wikipedia.png"> <link rel="icon" href="/static/favicon/wikipedia.ico"> <link rel="search" type="application/opensearchdescription+xml" href="/w/rest.php/v1/search" title="Wikipedia (en)"> <link rel="EditURI" type="application/rsd+xml" href="//en.wikipedia.org/w/api.php?action=rsd"> <link rel="canonical" href="https://en.wikipedia.org/wiki/Larock_indole_synthesis"> <link rel="license" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en"> <link rel="alternate" type="application/atom+xml" title="Wikipedia Atom feed" href="/w/index.php?title=Special:RecentChanges&feed=atom"> <link rel="dns-prefetch" href="//meta.wikimedia.org" /> <link rel="dns-prefetch" href="//login.wikimedia.org"> </head> <body class="skin--responsive skin-vector skin-vector-search-vue mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject mw-editable page-Larock_indole_synthesis rootpage-Larock_indole_synthesis skin-vector-2022 action-view"><a class="mw-jump-link" href="#bodyContent">Jump to content</a> <div class="vector-header-container"> <header class="vector-header mw-header"> <div class="vector-header-start"> <nav class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-dropdown" class="vector-dropdown vector-main-menu-dropdown vector-button-flush-left vector-button-flush-right" > <input type="checkbox" id="vector-main-menu-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-main-menu-dropdown" class="vector-dropdown-checkbox " aria-label="Main menu" > <label id="vector-main-menu-dropdown-label" for="vector-main-menu-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-menu mw-ui-icon-wikimedia-menu"></span> <span class="vector-dropdown-label-text">Main menu</span> </label> <div class="vector-dropdown-content"> <div id="vector-main-menu-unpinned-container" class="vector-unpinned-container"> <div id="vector-main-menu" class="vector-main-menu vector-pinnable-element"> <div class="vector-pinnable-header vector-main-menu-pinnable-header vector-pinnable-header-unpinned" data-feature-name="main-menu-pinned" data-pinnable-element-id="vector-main-menu" data-pinned-container-id="vector-main-menu-pinned-container" data-unpinned-container-id="vector-main-menu-unpinned-container" > <div class="vector-pinnable-header-label">Main menu</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-main-menu.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-main-menu.unpin">hide</button> </div> <div id="p-navigation" class="vector-menu mw-portlet mw-portlet-navigation" > <div class="vector-menu-heading"> Navigation </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-mainpage-description" class="mw-list-item"><a href="/wiki/Main_Page" title="Visit the main page [z]" accesskey="z"><span>Main page</span></a></li><li id="n-contents" class="mw-list-item"><a href="/wiki/Wikipedia:Contents" title="Guides to browsing Wikipedia"><span>Contents</span></a></li><li id="n-currentevents" class="mw-list-item"><a href="/wiki/Portal:Current_events" title="Articles related to current events"><span>Current events</span></a></li><li id="n-randompage" class="mw-list-item"><a href="/wiki/Special:Random" title="Visit a randomly selected article [x]" accesskey="x"><span>Random article</span></a></li><li id="n-aboutsite" class="mw-list-item"><a href="/wiki/Wikipedia:About" title="Learn about Wikipedia and how it works"><span>About Wikipedia</span></a></li><li id="n-contactpage" class="mw-list-item"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us" title="How to contact Wikipedia"><span>Contact us</span></a></li> </ul> </div> </div> <div id="p-interaction" class="vector-menu mw-portlet mw-portlet-interaction" > <div class="vector-menu-heading"> Contribute </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-help" class="mw-list-item"><a href="/wiki/Help:Contents" title="Guidance on how to use and edit Wikipedia"><span>Help</span></a></li><li id="n-introduction" class="mw-list-item"><a href="/wiki/Help:Introduction" title="Learn how to edit Wikipedia"><span>Learn to edit</span></a></li><li id="n-portal" class="mw-list-item"><a href="/wiki/Wikipedia:Community_portal" title="The hub for editors"><span>Community portal</span></a></li><li id="n-recentchanges" class="mw-list-item"><a href="/wiki/Special:RecentChanges" title="A list of recent changes to Wikipedia [r]" accesskey="r"><span>Recent changes</span></a></li><li id="n-upload" class="mw-list-item"><a href="/wiki/Wikipedia:File_upload_wizard" title="Add images or other media for use on Wikipedia"><span>Upload file</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> <a href="/wiki/Main_Page" class="mw-logo"> <img class="mw-logo-icon" src="/static/images/icons/wikipedia.png" alt="" aria-hidden="true" height="50" width="50"> <span class="mw-logo-container skin-invert"> <img class="mw-logo-wordmark" alt="Wikipedia" src="/static/images/mobile/copyright/wikipedia-wordmark-en.svg" style="width: 7.5em; height: 1.125em;"> <img class="mw-logo-tagline" alt="The Free Encyclopedia" src="/static/images/mobile/copyright/wikipedia-tagline-en.svg" width="117" height="13" style="width: 7.3125em; height: 0.8125em;"> </span> </a> </div> <div class="vector-header-end"> <div id="p-search" role="search" class="vector-search-box-vue vector-search-box-collapses vector-search-box-show-thumbnail vector-search-box-auto-expand-width vector-search-box"> <a href="/wiki/Special:Search" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only search-toggle" title="Search Wikipedia [f]" accesskey="f"><span class="vector-icon mw-ui-icon-search mw-ui-icon-wikimedia-search"></span> <span>Search</span> </a> <div class="vector-typeahead-search-container"> <div class="cdx-typeahead-search cdx-typeahead-search--show-thumbnail cdx-typeahead-search--auto-expand-width"> <form action="/w/index.php" id="searchform" class="cdx-search-input cdx-search-input--has-end-button"> <div id="simpleSearch" class="cdx-search-input__input-wrapper" data-search-loc="header-moved"> <div class="cdx-text-input cdx-text-input--has-start-icon"> <input class="cdx-text-input__input" type="search" name="search" placeholder="Search Wikipedia" aria-label="Search Wikipedia" autocapitalize="sentences" title="Search Wikipedia [f]" accesskey="f" id="searchInput" > <span class="cdx-text-input__icon cdx-text-input__start-icon"></span> </div> <input type="hidden" name="title" value="Special:Search"> </div> <button class="cdx-button cdx-search-input__end-button">Search</button> </form> </div> </div> </div> <nav class="vector-user-links vector-user-links-wide" aria-label="Personal tools"> <div class="vector-user-links-main"> <div id="p-vector-user-menu-preferences" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-userpage" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-dropdown" class="vector-dropdown " title="Change the appearance of the page's font size, width, and color" > <input type="checkbox" id="vector-appearance-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-appearance-dropdown" class="vector-dropdown-checkbox " aria-label="Appearance" > <label id="vector-appearance-dropdown-label" for="vector-appearance-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-appearance mw-ui-icon-wikimedia-appearance"></span> <span class="vector-dropdown-label-text">Appearance</span> </label> <div class="vector-dropdown-content"> <div id="vector-appearance-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <div id="p-vector-user-menu-notifications" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-overflow" class="vector-menu mw-portlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="https://donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_en.wikipedia.org&uselang=en" class=""><span>Donate</span></a> </li> <li id="pt-createaccount-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:CreateAccount&returnto=Larock+indole+synthesis" title="You are encouraged to create an account and log in; however, it is not mandatory" class=""><span>Create account</span></a> </li> <li id="pt-login-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:UserLogin&returnto=Larock+indole+synthesis" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o" class=""><span>Log in</span></a> </li> </ul> </div> </div> </div> <div id="vector-user-links-dropdown" class="vector-dropdown vector-user-menu vector-button-flush-right vector-user-menu-logged-out" title="Log in and more options" > <input type="checkbox" id="vector-user-links-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-user-links-dropdown" class="vector-dropdown-checkbox " aria-label="Personal tools" > <label id="vector-user-links-dropdown-label" for="vector-user-links-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-ellipsis mw-ui-icon-wikimedia-ellipsis"></span> <span class="vector-dropdown-label-text">Personal tools</span> </label> <div class="vector-dropdown-content"> <div id="p-personal" class="vector-menu mw-portlet mw-portlet-personal user-links-collapsible-item" title="User menu" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport" class="user-links-collapsible-item mw-list-item"><a href="https://donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_en.wikipedia.org&uselang=en"><span>Donate</span></a></li><li id="pt-createaccount" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:CreateAccount&returnto=Larock+indole+synthesis" title="You are encouraged to create an account and log in; however, it is not mandatory"><span class="vector-icon mw-ui-icon-userAdd mw-ui-icon-wikimedia-userAdd"></span> <span>Create account</span></a></li><li id="pt-login" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:UserLogin&returnto=Larock+indole+synthesis" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o"><span class="vector-icon mw-ui-icon-logIn mw-ui-icon-wikimedia-logIn"></span> <span>Log in</span></a></li> </ul> </div> </div> <div id="p-user-menu-anon-editor" class="vector-menu mw-portlet mw-portlet-user-menu-anon-editor" > <div class="vector-menu-heading"> Pages for logged out editors <a href="/wiki/Help:Introduction" aria-label="Learn more about editing"><span>learn more</span></a> </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-anoncontribs" class="mw-list-item"><a href="/wiki/Special:MyContributions" title="A list of edits made from this IP address [y]" accesskey="y"><span>Contributions</span></a></li><li id="pt-anontalk" class="mw-list-item"><a href="/wiki/Special:MyTalk" title="Discussion about edits from this IP address [n]" accesskey="n"><span>Talk</span></a></li> </ul> </div> </div> </div> </div> </nav> </div> </header> </div> <div class="mw-page-container"> <div class="mw-page-container-inner"> <div class="vector-sitenotice-container"> <div id="siteNotice"></div> </div> <div class="vector-column-start"> <div class="vector-main-menu-container"> <div id="mw-navigation"> <nav id="mw-panel" class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-pinned-container" class="vector-pinned-container"> </div> </nav> </div> </div> <div class="vector-sticky-pinned-container"> <nav id="mw-panel-toc" aria-label="Contents" data-event-name="ui.sidebar-toc" class="mw-table-of-contents-container vector-toc-landmark"> <div id="vector-toc-pinned-container" class="vector-pinned-container"> <div id="vector-toc" class="vector-toc vector-pinnable-element"> <div class="vector-pinnable-header vector-toc-pinnable-header vector-pinnable-header-pinned" data-feature-name="toc-pinned" data-pinnable-element-id="vector-toc" > <h2 class="vector-pinnable-header-label">Contents</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">hide</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">(Top)</div> </a> </li> <li id="toc-Overall_reaction" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Overall_reaction"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Overall reaction</span> </div> </a> <ul id="toc-Overall_reaction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reagents_and_optimal_conditions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reagents_and_optimal_conditions"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Reagents and optimal conditions</span> </div> </a> <button aria-controls="toc-Reagents_and_optimal_conditions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Reagents and optimal conditions subsection</span> </button> <ul id="toc-Reagents_and_optimal_conditions-sublist" class="vector-toc-list"> <li id="toc-Chlorides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chlorides"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Chlorides</span> </div> </a> <ul id="toc-Chlorides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Bases" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Bases"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Bases</span> </div> </a> <ul id="toc-Bases-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Alkynes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Alkynes"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Alkynes</span> </div> </a> <ul id="toc-Alkynes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-PPh3_as_a_catalyst" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#PPh3_as_a_catalyst"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>PPh<sub>3</sub> as a catalyst</span> </div> </a> <ul id="toc-PPh3_as_a_catalyst-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reaction_mechanism" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reaction_mechanism"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Reaction mechanism</span> </div> </a> <ul id="toc-Reaction_mechanism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Modifications_and_variations" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Modifications_and_variations"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Modifications and variations</span> </div> </a> <ul id="toc-Modifications_and_variations-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Applications</span> </div> </a> <ul id="toc-Applications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Larock indole synthesis</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 6 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-6" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">6 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Larock-Indolsynthese" title="Larock-Indolsynthese – German" lang="de" hreflang="de" data-title="Larock-Indolsynthese" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/S%C3%ADntesis_de_indoles_de_Larock" title="Síntesis de indoles de Larock – Spanish" lang="es" hreflang="es" data-title="Síntesis de indoles de Larock" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B3%D9%86%D8%AA%D8%B2_%D8%A7%DB%8C%D9%86%D8%AF%D9%88%D9%84_%D9%84%D8%A7%D8%B1%D9%88%DA%A9" title="سنتز ایندول لاروک – Persian" lang="fa" hreflang="fa" data-title="سنتز ایندول لاروک" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Synth%C3%A8se_d%27indole_de_Larock" title="Synthèse d'indole de Larock – French" lang="fr" hreflang="fr" data-title="Synthèse d'indole de Larock" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Larock-indoolsynthese" title="Larock-indoolsynthese – Dutch" lang="nl" hreflang="nl" data-title="Larock-indoolsynthese" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/Larock%E5%90%B2%E5%93%9A%E5%90%88%E6%88%90" title="Larock吲哚合成 – Chinese" lang="zh" hreflang="zh" data-title="Larock吲哚合成" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q2783827#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Larock_indole_synthesis" title="View the content page [c]" accesskey="c"><span>Article</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Talk:Larock_indole_synthesis" rel="discussion" title="Discuss improvements to the content page [t]" accesskey="t"><span>Talk</span></a></li> </ul> </div> </div> <div id="vector-variants-dropdown" class="vector-dropdown emptyPortlet" > <input type="checkbox" id="vector-variants-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-variants-dropdown" class="vector-dropdown-checkbox " aria-label="Change language variant" > <label id="vector-variants-dropdown-label" for="vector-variants-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">English</span> </label> <div class="vector-dropdown-content"> <div id="p-variants" class="vector-menu mw-portlet mw-portlet-variants emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> </div> </div> </nav> </div> <div id="right-navigation" class="vector-collapsible"> <nav aria-label="Views"> <div id="p-views" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-views" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-view" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Larock_indole_synthesis"><span>Read</span></a></li><li id="ca-edit" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Larock_indole_synthesis&action=edit" title="Edit this page [e]" accesskey="e"><span>Edit</span></a></li><li id="ca-history" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Larock_indole_synthesis&action=history" title="Past revisions of this page [h]" accesskey="h"><span>View history</span></a></li> </ul> </div> </div> </nav> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-dropdown" class="vector-dropdown vector-page-tools-dropdown" > <input type="checkbox" id="vector-page-tools-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-tools-dropdown" class="vector-dropdown-checkbox " aria-label="Tools" > <label id="vector-page-tools-dropdown-label" for="vector-page-tools-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">Tools</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-tools-unpinned-container" class="vector-unpinned-container"> <div id="vector-page-tools" class="vector-page-tools vector-pinnable-element"> <div class="vector-pinnable-header vector-page-tools-pinnable-header vector-pinnable-header-unpinned" data-feature-name="page-tools-pinned" data-pinnable-element-id="vector-page-tools" data-pinned-container-id="vector-page-tools-pinned-container" data-unpinned-container-id="vector-page-tools-unpinned-container" > <div class="vector-pinnable-header-label">Tools</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-page-tools.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-page-tools.unpin">hide</button> </div> <div id="p-cactions" class="vector-menu mw-portlet mw-portlet-cactions emptyPortlet vector-has-collapsible-items" title="More options" > <div class="vector-menu-heading"> Actions </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-more-view" class="selected vector-more-collapsible-item mw-list-item"><a href="/wiki/Larock_indole_synthesis"><span>Read</span></a></li><li id="ca-more-edit" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Larock_indole_synthesis&action=edit" title="Edit this page [e]" accesskey="e"><span>Edit</span></a></li><li id="ca-more-history" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Larock_indole_synthesis&action=history"><span>View history</span></a></li> </ul> </div> </div> <div id="p-tb" class="vector-menu mw-portlet mw-portlet-tb" > <div class="vector-menu-heading"> General </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="t-whatlinkshere" class="mw-list-item"><a href="/wiki/Special:WhatLinksHere/Larock_indole_synthesis" title="List of all English Wikipedia pages containing links to this page [j]" accesskey="j"><span>What links here</span></a></li><li id="t-recentchangeslinked" class="mw-list-item"><a href="/wiki/Special:RecentChangesLinked/Larock_indole_synthesis" rel="nofollow" title="Recent changes in pages linked from this page [k]" accesskey="k"><span>Related changes</span></a></li><li id="t-upload" class="mw-list-item"><a href="/wiki/Wikipedia:File_Upload_Wizard" title="Upload files [u]" accesskey="u"><span>Upload file</span></a></li><li id="t-specialpages" class="mw-list-item"><a href="/wiki/Special:SpecialPages" title="A list of all special pages [q]" accesskey="q"><span>Special pages</span></a></li><li id="t-permalink" class="mw-list-item"><a href="/w/index.php?title=Larock_indole_synthesis&oldid=1173388557" title="Permanent link to this revision of this page"><span>Permanent link</span></a></li><li id="t-info" class="mw-list-item"><a href="/w/index.php?title=Larock_indole_synthesis&action=info" title="More information about this page"><span>Page information</span></a></li><li id="t-cite" class="mw-list-item"><a href="/w/index.php?title=Special:CiteThisPage&page=Larock_indole_synthesis&id=1173388557&wpFormIdentifier=titleform" title="Information on how to cite this page"><span>Cite this page</span></a></li><li id="t-urlshortener" class="mw-list-item"><a href="/w/index.php?title=Special:UrlShortener&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FLarock_indole_synthesis"><span>Get shortened URL</span></a></li><li id="t-urlshortener-qrcode" class="mw-list-item"><a href="/w/index.php?title=Special:QrCode&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FLarock_indole_synthesis"><span>Download QR code</span></a></li> </ul> </div> </div> <div id="p-coll-print_export" class="vector-menu mw-portlet mw-portlet-coll-print_export" > <div class="vector-menu-heading"> Print/export </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="coll-download-as-rl" class="mw-list-item"><a href="/w/index.php?title=Special:DownloadAsPdf&page=Larock_indole_synthesis&action=show-download-screen" title="Download this page as a PDF file"><span>Download as PDF</span></a></li><li id="t-print" class="mw-list-item"><a href="/w/index.php?title=Larock_indole_synthesis&printable=yes" title="Printable version of this page [p]" accesskey="p"><span>Printable version</span></a></li> </ul> </div> </div> <div id="p-wikibase-otherprojects" class="vector-menu mw-portlet mw-portlet-wikibase-otherprojects" > <div class="vector-menu-heading"> In other projects </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="wb-otherproject-link wb-otherproject-commons mw-list-item"><a href="https://commons.wikimedia.org/wiki/Category:Larock_indole_synthesis" hreflang="en"><span>Wikimedia Commons</span></a></li><li id="t-wikibase" class="wb-otherproject-link wb-otherproject-wikibase-dataitem mw-list-item"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q2783827" title="Structured data on this page hosted by Wikidata [g]" accesskey="g"><span>Wikidata item</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Heteroannulation reaction</div> <style data-mw-deduplicate="TemplateStyles:r1049416944">.mw-parser-output .ib-reactionbox{border-collapse:collapse}.mw-parser-output .ib-reactionbox td,.mw-parser-output .ib-reactionbox th{border:1px solid #a2a9b1}</style> <table class="infobox ib-reactionbox"> <tbody><tr> <th style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2">Larock indole synthesis </th></tr> <tr> <td>Named after </td> <td>Richard C. Larock </td></tr> <tr> <td>Reaction type </td> <td><a href="/wiki/Ring_forming_reaction" title="Ring forming reaction">Ring forming reaction</a> </td></tr> <tr> <th style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2">Identifiers </th></tr> <tr> <td><a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">RSC</a> ontology ID </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/ols/ontologies/rxno/terms?iri=http%3A%2F%2Fpurl.obolibrary.org%2Fobo%2FRXNO_0000396">RXNO:0000396</a></span> </td></tr> <tr> <td style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2"> </td></tr> </tbody></table> <p>The <b>Larock indole synthesis</b> is a hetero<a href="/wiki/Annulation" title="Annulation">annulation</a> reaction that uses <a href="/wiki/Palladium" title="Palladium">palladium</a> as a catalyst to synthesize <a href="/wiki/Indole" title="Indole">indoles</a> from an ortho-iodo<a href="/wiki/Aniline" title="Aniline">aniline</a> and a disubstituted <a href="/wiki/Alkyne" title="Alkyne">alkyne</a>.<sup id="cite_ref-r1_1-0" class="reference"><a href="#cite_note-r1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> It is also known as Larock hetero<a href="/wiki/Annulation" title="Annulation">annulation</a>. The reaction is extremely versatile and can be used to produce varying types of indoles. Larock indole synthesis was first proposed by Richard C. Larock in 1991 at <a href="/wiki/Iowa_State_University" title="Iowa State University">Iowa State University</a>.<sup id="cite_ref-li_2-0" class="reference"><a href="#cite_note-li-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Larock_Indole_Synthesis_Scheme.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Larock_Indole_Synthesis_Scheme.png/380px-Larock_Indole_Synthesis_Scheme.png" decoding="async" width="380" height="115" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Larock_Indole_Synthesis_Scheme.png/570px-Larock_Indole_Synthesis_Scheme.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/46/Larock_Indole_Synthesis_Scheme.png/760px-Larock_Indole_Synthesis_Scheme.png 2x" data-file-width="1132" data-file-height="342" /></a><figcaption>The Larock indole synthesis</figcaption></figure> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Overall_reaction">Overall reaction</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Larock_indole_synthesis&action=edit&section=1" title="Edit section: Overall reaction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The reaction usually occurs with an <i>o</i>-iodianiline or its derivatives, 2–5 equivalents of an alkyne, palladium(II) (PdII), an excess of sodium or potassium carbonate base, PPh<sub>3</sub>, and 1 equivalent of LiCl or n-Bu<sub>4</sub>NCl. N-methyl, N-acetyl, and N-tosyl derivatives of ortho-iodoanilines have been shown to be the most successful anilines that can be used to produce good to excellent yields.<sup id="cite_ref-r2_3-0" class="reference"><a href="#cite_note-r2-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Reagents_and_optimal_conditions">Reagents and optimal conditions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Larock_indole_synthesis&action=edit&section=2" title="Edit section: Reagents and optimal conditions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Chlorides">Chlorides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Larock_indole_synthesis&action=edit&section=3" title="Edit section: Chlorides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Either LiCl or n-Bu<sub>4</sub>N are used depending on the reaction conditions, but LiCl appears to be the more effective base in Larock indole annulation.<sup id="cite_ref-r2_3-1" class="reference"><a href="#cite_note-r2-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The stoichiometry of LiCl is also considerably important, as more than 1 equivalent of LiCl will slow the rate of reaction and lower the overall yield.<sup id="cite_ref-r1_1-1" class="reference"><a href="#cite_note-r1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Bases">Bases</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Larock_indole_synthesis&action=edit&section=4" title="Edit section: Bases"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Bases other than sodium or potassium carbonate have been used to produce a good overall yield of the annulation reaction.<sup id="cite_ref-r2_3-2" class="reference"><a href="#cite_note-r2-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> For example, KOAc can be used with 1 equivalent of LiCl. However, the reaction using KOAc must be used at 120 °C to reach completion of the reaction at a reasonable time. In contrast K<sub>2</sub>CO<sub>3</sub> can be used at 100 °C. </p> <div class="mw-heading mw-heading3"><h3 id="Alkynes">Alkynes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Larock_indole_synthesis&action=edit&section=5" title="Edit section: Alkynes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The Larock indole synthesis is a flexible reaction partly due to the variety of substituted alkynes that can be used in the annulation reaction. In particular, alkynes with substituents including alkyls, aryls, alkenyls, hydroxyls, and silyls have been successfully used.<sup id="cite_ref-r2_3-3" class="reference"><a href="#cite_note-r2-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> However, bulkier tertiary alkyl or trimethylsilyl groups have been shown to provide a higher yield.<sup id="cite_ref-r1_1-2" class="reference"><a href="#cite_note-r1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The annulation reaction will also proceed more efficiently when 2–5 equivalents of an alkyne is used. Less than two equivalents appear to create suboptimal conditions for the reaction. </p> <div class="mw-heading mw-heading3"><h3 id="PPh3_as_a_catalyst">PPh<sub>3</sub> as a catalyst</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Larock_indole_synthesis&action=edit&section=6" title="Edit section: PPh3 as a catalyst"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>5% mol of PPh<sub>3</sub> was initially used in the reaction as a catalyst.<sup id="cite_ref-r1_1-3" class="reference"><a href="#cite_note-r1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> However, later experiments have shown that PPh<sub>3</sub> does not significantly improve the overall yield and is not necessary.<sup id="cite_ref-r2_3-4" class="reference"><a href="#cite_note-r2-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Reaction_mechanism">Reaction mechanism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Larock_indole_synthesis&action=edit&section=7" title="Edit section: Reaction mechanism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The Larock indole synthesis proceeds via the following intermediate steps:<sup id="cite_ref-r2_3-5" class="reference"><a href="#cite_note-r2-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <ol><li>Pd(OAc)2 is reduced to Pd(0).</li> <li>A coordination of the chloride occurs to form a chloride-ligated zerovalent palladium.</li> <li>The <i>o</i>-iodoaniline undergoes oxidative addition to Pd(II).</li> <li>The alkyne coordinates to the Pd(II) by ligand exchange.</li> <li>A migratory insertion causes the alkyne to undergo regioselective syn-insertion into arylpalladium bond. Regioselectivity is determined during this step.</li> <li>The nitrogen displaces the halide in the resulting vinylic palladium intermediate to form the six-membered palladium-containing heteroatom.</li> <li>The Pd(II) center undergoes a reductive elimination to form the indole and regenerate Pd(0) which can then be recycled into the catalytic indole process.</li></ol> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Mechanism_of_the_Larock_Indole_Synthesis.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Mechanism_of_the_Larock_Indole_Synthesis.jpg/450px-Mechanism_of_the_Larock_Indole_Synthesis.jpg" decoding="async" width="450" height="470" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/7/7e/Mechanism_of_the_Larock_Indole_Synthesis.jpg 1.5x" data-file-width="519" data-file-height="542" /></a><figcaption>Larock indole synthesis mechanism.<sup id="cite_ref-r2_3-6" class="reference"><a href="#cite_note-r2-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>The carbopalladation step is regioselective when unsymmetrical alkynes are used.<sup id="cite_ref-r1_1-4" class="reference"><a href="#cite_note-r1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-r2_3-7" class="reference"><a href="#cite_note-r2-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Although it was previously believed that the alkyne is inserted with the less sterically-hindering R-group adjacent to the arylpalladium, Larock et al. observed that the larger more sterically-hindering R-group is inserted next to the arylpalladium.<sup id="cite_ref-r1_1-5" class="reference"><a href="#cite_note-r1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> They suggest that the driving force of the alkyne insertion may be the steric hindrance present in the developing carbon-carbon bond and the orientation of the alkyne prior to syn-insertion of the alkyne into the aryl palladium bond.<sup id="cite_ref-r2_3-8" class="reference"><a href="#cite_note-r2-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Alkyne insertion occurs so that the large substituent on the alkyne avoids steric strain from the short developing carbon-carbon bond by interacting with the longer carbon-palladium bond. </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Showing_that_Larock_Indole_Synthesis_is_regioselective.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/3/3f/Showing_that_Larock_Indole_Synthesis_is_regioselective.jpg" decoding="async" width="367" height="136" class="mw-file-element" data-file-width="367" data-file-height="136" /></a><figcaption>Regioselectivity of the alkyne insertion in Larock indole synthesis<sup id="cite_ref-r2_3-9" class="reference"><a href="#cite_note-r2-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Modifications_and_variations">Modifications and variations</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Larock_indole_synthesis&action=edit&section=8" title="Edit section: Modifications and variations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><i>o</i>-bromoanilines or <i>o</i>-chloroanilines do not undergo Larock indole synthesis. However, researchers from Boehringer-Ingelheim were able to successfully use both <i>o</i>-bromoanilines and <i>o</i>-chloroanilines to form indoles by using <a href="/wiki/N-methyl-2-pyrrolidone" class="mw-redirect" title="N-methyl-2-pyrrolidone">N-methyl-2-pyrrolidone</a> (NMP) as the solvent with 1,1'bis(di-tert-butylphosphino)ferrocene as the palladium ligand.<sup id="cite_ref-Li_4-0" class="reference"><a href="#cite_note-Li-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> <i>O</i>-bromoanilines and <i>o</i>-chloroanilines are more readily available and cost-effective over using <i>o</i>-iodianiline in Larock indole synthesis.<sup id="cite_ref-li_2-1" class="reference"><a href="#cite_note-li-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Heterannulation_using_o-chloroaniline_derivative.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/7/75/Heterannulation_using_o-chloroaniline_derivative.jpg" decoding="async" width="397" height="328" class="mw-file-element" data-file-width="397" data-file-height="328" /></a><figcaption>Heterannulation of an indole using <i>o</i>-chloroaniline<sup id="cite_ref-Li_4-1" class="reference"><a href="#cite_note-Li-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>Monguchi et al. also derived 2- and 2,3-substituted indoles without using LiCl.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> The optimized Indole reaction uses 10% Pd/C (3.0 mol%) with 1.1 equivalent of NaOAc, and NMP at 110–130 °C. Monguchi et al. state that their optimized condition of the Larock indole synthesis without LiCl is a more mild, environmentally benign, and efficient strategy for producing indoles. </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Larock_indole_synthesis&action=edit&section=9" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Indole" title="Indole">Indoles</a> are one of the most prevalent heterocyclic structures found in biological processes, so the production of indole derivatives are important in a diversity of fields. </p><p>Nishikawa et al. derived iso-tryptophan by using Larock indole synthesis with pre-synthesized α-C-glucosylpropargyl glycine and o-iodo-tosylanilide.<sup id="cite_ref-Nishikawa_6-0" class="reference"><a href="#cite_note-Nishikawa-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> This reaction produced the product which had the reverse regioselectivity of normal Larock indole synthesis. The larger substituent was placed adjacent to the forming carbon-carbon bond, rather than the carbon-palladium bond. The explanation for the reverse regioselectivity which produced the iso-tryptophan is unknown. </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Larock_Indole_Synthesis_of_alpha-C-Glycosylamino_Acid_to_Iso-Tryptophan.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/d/dc/Larock_Indole_Synthesis_of_alpha-C-Glycosylamino_Acid_to_Iso-Tryptophan.jpg" decoding="async" width="472" height="296" class="mw-file-element" data-file-width="472" data-file-height="296" /></a><figcaption>Larock indole synthesis of iso-tryptophan using α-<i>C</i>-glycosylamino acid<sup id="cite_ref-Nishikawa_6-1" class="reference"><a href="#cite_note-Nishikawa-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>Optically active tryptophan which adheres to the regioselectivity of the Larock indole synthesis can also be synthesized using o-iodoaniline with propargyl substituted bislactim ethyl ether. Propargyl substituted bislactim ethyl ether is generated by using Schöllkopf chiral auxiliary bis lactam ether with n-BuLi, THF, and 3-halo-1-9trimethylsily1)-1-propyne and extracting the trans-isomer of the propargyl-substituted bislactim.<sup id="cite_ref-Ma_7-0" class="reference"><a href="#cite_note-Ma-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:A_reaction_using_Larock_Indole_Synthesis_to_produce_chirally_active_tryptophan.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/91/A_reaction_using_Larock_Indole_Synthesis_to_produce_chirally_active_tryptophan.jpg/450px-A_reaction_using_Larock_Indole_Synthesis_to_produce_chirally_active_tryptophan.jpg" decoding="async" width="450" height="452" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/9/91/A_reaction_using_Larock_Indole_Synthesis_to_produce_chirally_active_tryptophan.jpg 1.5x" data-file-width="508" data-file-height="510" /></a><figcaption>Chirally active tryptophan by Larock indole synthesis<sup id="cite_ref-Ma_7-1" class="reference"><a href="#cite_note-Ma-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>Other relevant applications include the synthesis of 5-HT<sub>1D</sub> receptor agonist MK-0462, an anti-<a href="/wiki/Migraine" title="Migraine">migraine</a> drug.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Larock_indole_synthesis&action=edit&section=10" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-r1-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-r1_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-r1_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-r1_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-r1_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-r1_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-r1_1-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFLarockYum1991" class="citation journal cs1">Larock, R. C.; Yum, E. K. (1991). "Synthesis of indoles via palladium-catalyzed heteroannulation of internal alkynes". <i>Journal of the American Chemical Society</i>. <b>113</b> (17): 6689. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja00017a059">10.1021/ja00017a059</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.atitle=Synthesis+of+indoles+via+palladium-catalyzed+heteroannulation+of+internal+alkynes&rft.volume=113&rft.issue=17&rft.pages=6689&rft.date=1991&rft_id=info%3Adoi%2F10.1021%2Fja00017a059&rft.aulast=Larock&rft.aufirst=R.+C.&rft.au=Yum%2C+E.+K.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALarock+indole+synthesis" class="Z3988"></span></span> </li> <li id="cite_note-li-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-li_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-li_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">Li, J.J. (2011) "Larock Indole Synthesis" in <i>Name Reactions in Heterocyclic Chemistry II</i>, John Wiley & Sons, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-08508-0" title="Special:BookSources/978-0-470-08508-0">978-0-470-08508-0</a>, pp. 143–166.</span> </li> <li id="cite_note-r2-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-r2_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-r2_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-r2_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-r2_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-r2_3-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-r2_3-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-r2_3-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-r2_3-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-r2_3-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-r2_3-9"><sup><i><b>j</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLarockYumRefvik1998" class="citation journal cs1">Larock, R. C.; Yum, E. K.; Refvik, M. D. (1998). "Synthesis of 2,3-Disubstituted Indoles via Palladium-Catalyzed Annulation of Internal Alkynes". <i>The Journal of Organic Chemistry</i>. <b>63</b> (22): 7652. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo9803277">10.1021/jo9803277</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Organic+Chemistry&rft.atitle=Synthesis+of+2%2C3-Disubstituted+Indoles+via+Palladium-Catalyzed+Annulation+of+Internal+Alkynes&rft.volume=63&rft.issue=22&rft.pages=7652&rft.date=1998&rft_id=info%3Adoi%2F10.1021%2Fjo9803277&rft.aulast=Larock&rft.aufirst=R.+C.&rft.au=Yum%2C+E.+K.&rft.au=Refvik%2C+M.+D.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALarock+indole+synthesis" class="Z3988"></span></span> </li> <li id="cite_note-Li-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-Li_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Li_4-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">Li, G., Liu, J., Lu, B., Roschangar, F., Senanayake, C.H., Shen, M. (2005) "By reacting with substituted acetylenes in the presence of a phosphine ligand and a base (K<sub>2</sub>CO<sub>3</sub>); used to make drugs" <span><a rel="nofollow" class="external text" href="https://patents.google.com/patent/US20050209465">U.S. patent 20,050,209,465</a></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMonguchiMoriAoyagiTsutsui2010" class="citation journal cs1">Monguchi, Y.; Mori, S.; Aoyagi, S.; Tsutsui, A.; Maegawa, T.; Sajiki, H. (2010). "Palladium on carbon-catalyzed synthesis of 2- and 2,3-substituted indoles under heterogeneous conditions". <i>Organic & Biomolecular Chemistry</i>. <b>8</b> (14): 3338–42. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fc004939e">10.1039/c004939e</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20526486">20526486</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+%26+Biomolecular+Chemistry&rft.atitle=Palladium+on+carbon-catalyzed+synthesis+of+2-+and+2%2C3-substituted+indoles+under+heterogeneous+conditions&rft.volume=8&rft.issue=14&rft.pages=3338-42&rft.date=2010&rft_id=info%3Adoi%2F10.1039%2Fc004939e&rft_id=info%3Apmid%2F20526486&rft.aulast=Monguchi&rft.aufirst=Y.&rft.au=Mori%2C+S.&rft.au=Aoyagi%2C+S.&rft.au=Tsutsui%2C+A.&rft.au=Maegawa%2C+T.&rft.au=Sajiki%2C+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALarock+indole+synthesis" class="Z3988"></span></span> </li> <li id="cite_note-Nishikawa-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-Nishikawa_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Nishikawa_6-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNishikawaWadaIsobe2002" class="citation journal cs1">Nishikawa, T.; Wada, K.; Isobe, M. (2002). "Synthesis of Novel .ALPHA.-C-Glycosylamino Acids and Reverse Regioselectivity in Larock's Heteroannulation for the Synthesis of the Indole Nucleus". <i>Bioscience, Biotechnology, and Biochemistry</i>. <b>66</b> (10): 2273–8. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1271%2Fbbb.66.2273">10.1271/bbb.66.2273</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12450149">12450149</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bioscience%2C+Biotechnology%2C+and+Biochemistry&rft.atitle=Synthesis+of+Novel+.ALPHA.-C-Glycosylamino+Acids+and+Reverse+Regioselectivity+in+Larock%27s+Heteroannulation+for+the+Synthesis+of+the+Indole+Nucleus&rft.volume=66&rft.issue=10&rft.pages=2273-8&rft.date=2002&rft_id=info%3Adoi%2F10.1271%2Fbbb.66.2273&rft_id=info%3Apmid%2F12450149&rft.aulast=Nishikawa&rft.aufirst=T.&rft.au=Wada%2C+K.&rft.au=Isobe%2C+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALarock+indole+synthesis" class="Z3988"></span></span> </li> <li id="cite_note-Ma-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ma_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ma_7-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMaLiuYuZhao1999" class="citation journal cs1">Ma, C.; Liu, X.; Yu, S.; Zhao, S.; Cook, J. M. (1999). "Concise synthesis of optically active ring-A substituted tryptophans". <i>Tetrahedron Letters</i>. <b>40</b> (4): 657. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0040-4039%2898%2902497-6">10.1016/S0040-4039(98)02497-6</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Letters&rft.atitle=Concise+synthesis+of+optically+active+ring-A+substituted+tryptophans&rft.volume=40&rft.issue=4&rft.pages=657&rft.date=1999&rft_id=info%3Adoi%2F10.1016%2FS0040-4039%2898%2902497-6&rft.aulast=Ma&rft.aufirst=C.&rft.au=Liu%2C+X.&rft.au=Yu%2C+S.&rft.au=Zhao%2C+S.&rft.au=Cook%2C+J.+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALarock+indole+synthesis" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChen,_C.-Y,_Lieberman,_D.R.,_Larsen,_R.D.,_Reamer,_R.A.,_Verhoeven,_T.R.,_Reider,_P.J.,_Cottrell,_I.F.,_Houghton,_P.G.1994" class="citation journal cs1">Chen, C.-Y, Lieberman, D.R., Larsen, R.D., Reamer, R.A., Verhoeven, T.R., Reider, P.J., Cottrell, I.F., Houghton, P.G. (1994). "Synthesis of the 5-HT<sub>1D</sub> agonist MK-0462 via a Pd-catalyzed coupling reaction". <i><a href="/wiki/Tetrahedron_Lett." class="mw-redirect" title="Tetrahedron Lett.">Tetrahedron Lett.</a></i> <b>35</b>: 6981–6984. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0040-4039%2894%2988204-5">10.1016/0040-4039(94)88204-5</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Lett.&rft.atitle=Synthesis+of+the+5-HT%3Csub%3E1D%3C%2Fsub%3E+agonist+MK-0462+via+a+Pd-catalyzed+coupling+reaction&rft.volume=35&rft.pages=6981-6984&rft.date=1994&rft_id=info%3Adoi%2F10.1016%2F0040-4039%2894%2988204-5&rft.au=Chen%2C+C.-Y%2C+Lieberman%2C+D.R.%2C+Larsen%2C+R.D.%2C+Reamer%2C+R.A.%2C+Verhoeven%2C+T.R.%2C+Reider%2C+P.J.%2C+Cottrell%2C+I.F.%2C+Houghton%2C+P.G.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALarock+indole+synthesis" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> </ol></div></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Larock_indole_synthesis&oldid=1173388557">https://en.wikipedia.org/w/index.php?title=Larock_indole_synthesis&oldid=1173388557</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Ring_forming_reactions" title="Category:Ring forming reactions">Ring forming reactions</a></li><li><a href="/wiki/Category:Indole_forming_reactions" title="Category:Indole forming reactions">Indole forming reactions</a></li><li><a href="/wiki/Category:Name_reactions" title="Category:Name reactions">Name reactions</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">CS1 maint: multiple names: authors list</a></li><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches Wikidata</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 2 September 2023, at 03:15<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. By using this site, you agree to the <a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Terms_of_Use" class="extiw" title="foundation:Special:MyLanguage/Policy:Terms of Use">Terms of Use</a> and <a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy" class="extiw" title="foundation:Special:MyLanguage/Policy:Privacy policy">Privacy Policy</a>. Wikipedia® is a registered trademark of the <a rel="nofollow" class="external text" href="https://wikimediafoundation.org/">Wikimedia Foundation, Inc.</a>, a non-profit organization.</li> </ul> <ul id="footer-places"> <li id="footer-places-privacy"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy">Privacy policy</a></li> <li id="footer-places-about"><a href="/wiki/Wikipedia:About">About Wikipedia</a></li> <li id="footer-places-disclaimers"><a href="/wiki/Wikipedia:General_disclaimer">Disclaimers</a></li> <li id="footer-places-contact"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us">Contact Wikipedia</a></li> <li id="footer-places-wm-codeofconduct"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Universal_Code_of_Conduct">Code of Conduct</a></li> <li id="footer-places-developers"><a href="https://developer.wikimedia.org">Developers</a></li> <li id="footer-places-statslink"><a href="https://stats.wikimedia.org/#/en.wikipedia.org">Statistics</a></li> <li id="footer-places-cookiestatement"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Cookie_statement">Cookie statement</a></li> <li id="footer-places-mobileview"><a href="//en.m.wikipedia.org/w/index.php?title=Larock_indole_synthesis&mobileaction=toggle_view_mobile" class="noprint stopMobileRedirectToggle">Mobile view</a></li> </ul> <ul id="footer-icons" class="noprint"> <li id="footer-copyrightico"><a href="https://wikimediafoundation.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><img src="/static/images/footer/wikimedia-button.svg" width="84" height="29" alt="Wikimedia Foundation" loading="lazy"></a></li> <li id="footer-poweredbyico"><a href="https://www.mediawiki.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><img src="/w/resources/assets/poweredby_mediawiki.svg" alt="Powered by MediaWiki" width="88" height="31" loading="lazy"></a></li> </ul> </footer> </div> </div> </div> <div class="vector-settings" id="p-dock-bottom"> <ul></ul> </div><script>(RLQ=window.RLQ||[]).push(function(){mw.config.set({"wgHostname":"mw-web.codfw.canary-84779d6bf6-wmcb5","wgBackendResponseTime":119,"wgPageParseReport":{"limitreport":{"cputime":"0.242","walltime":"0.347","ppvisitednodes":{"value":1206,"limit":1000000},"postexpandincludesize":{"value":17896,"limit":2097152},"templateargumentsize":{"value":1372,"limit":2097152},"expansiondepth":{"value":16,"limit":100},"expensivefunctioncount":{"value":2,"limit":500},"unstrip-depth":{"value":1,"limit":20},"unstrip-size":{"value":30884,"limit":5000000},"entityaccesscount":{"value":0,"limit":400},"timingprofile":["100.00% 286.751 1 -total"," 56.62% 162.372 1 Template:Reflist"," 39.24% 112.520 6 Template:Cite_journal"," 27.12% 77.780 1 Template:Short_description"," 15.37% 44.078 2 Template:Pagetype"," 11.67% 33.468 1 Template:Reactionbox"," 7.48% 21.451 5 Template:Main_other"," 6.42% 18.422 1 Template:SDcat"," 6.24% 17.907 1 Template:ISBN"," 4.06% 11.633 1 Template:US_Patent"]},"scribunto":{"limitreport-timeusage":{"value":"0.114","limit":"10.000"},"limitreport-memusage":{"value":4198241,"limit":52428800}},"cachereport":{"origin":"mw-web.eqiad.main-5dc468848-wb7jj","timestamp":"20241122144936","ttl":2592000,"transientcontent":false}}});});</script> <script type="application/ld+json">{"@context":"https:\/\/schema.org","@type":"Article","name":"Larock indole synthesis","url":"https:\/\/en.wikipedia.org\/wiki\/Larock_indole_synthesis","sameAs":"http:\/\/www.wikidata.org\/entity\/Q2783827","mainEntity":"http:\/\/www.wikidata.org\/entity\/Q2783827","author":{"@type":"Organization","name":"Contributors to Wikimedia projects"},"publisher":{"@type":"Organization","name":"Wikimedia Foundation, Inc.","logo":{"@type":"ImageObject","url":"https:\/\/www.wikimedia.org\/static\/images\/wmf-hor-googpub.png"}},"datePublished":"2005-08-05T03:02:14Z","dateModified":"2023-09-02T03:15:27Z","headline":"heteroannulation reaction"}</script> </body> </html>