Thieme E-Journals - Synthesis / Abstract

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<span class="articleCategories">© Georg Thieme Verlag Stuttgart · New York</span> <h1>Catalytic Hydration of Alkynes and Its Application in Synthesis</h1> <span class="authors">Lukas Hintermann*, Aurélie Labonne<br>Institut für Organische Chemie, RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany<BR>Fax: +49(241)8092391; e-Mail: <A HREF="mailto:lukas.hintermann@oc.rwth-aachen.de">lukas.hintermann@oc.rwth-aachen.de</A>; <BR> </span> <div class="toggleMenu articleToggleMenu"> <div class="toggleButton">Further Information<div class="toggleContent"> <div class="wrapper twoCols"> <div class="col"> <h3>Publication History</h3> <p> <TR> <TD COLSPAN="2"><EM CLASS="ITALIC"> Received 31 January 2007</EM></TD> </TR> <br>Publication Date:<br>23 March 2007 (online)</p> </div> </div> </div> </div> </div> </div><ul class="tabBar borderBottom" id="articleTabs"> <li class="tab active"> <a href="#abstract">Abstract</a> </li> <li class="tab"> <a href="/products/ejournals/html/10.1055/s-2007-966002">Full Text</a> </li> <li class="tab"> <a href="#references">References</a> </li> </ul><div id="sections"> <section id="abstract"> <div class="articleFunctions"> <input value="ai10.1055/s-2007-966002,10.1055/s-2007-966002" name="ai" type="hidden"> <div style="display: none" id="sfx10.1055/s-2007-966002"> <a id="sfxServer" data-href="?id=doi:10.1055/s-2007-966002&sid=Thieme:Connect&jtitle=Synthesis&issue=08&volume=2007&date=2007&issn=0039-7881&spage=1121&epage=1150&aulast=Hintermann&aufirst=Lukas&__char_set=utf8&atitle=Catalytic Hydration of Alkynes and Its Application in Synthesis" target="sfx"><span class="articleAccessLabel sfx"><img id="sfxImageUrl" src="" alt="SFX Search" height="15" width="52"></span></a> </div> <a style="display: none" href="/products/ejournals/buyDocument/10.1055/s-2007-966002" class="gotoLink" id="sasLink">Buy Article</a> <a data-url="https://s100.copyright.com/AppDispatchServlet" data-id="CCC RightsLink" data-target="CCC RightsLink" onClick="RightslinkPopUp("1437-210X", "Catalytic Hydration of Alkynes and Its Application in Synthesis", "03/23/2007", "Lukas Hintermann, Aurélie Labonne", "", "10.1055/s-2007-966002", "1121", "1150", "2007", "08", "")" class="gotoLink linkFunction" href="javascript:;">Permissions and Reprints</a> <a class="gotoLink" href="/products/ejournals/category/000082/10.1055/s-00000084">All articles of this category</a> </div> <figure style="margin-left: 30px" class="floatRight"> <a data-doi="10.1055/s-2007-966002" data-caption="" data-id="10.1055-s-2007-966002-1.jpg" data-cssClass="previewOverlay" href="https://www.thieme-connect.de/media/synthesis/200708/lookinside/10.1055-s-2007-966002-1.jpg" class="zoomFunction alignLeft"><img src="https://www.thieme-connect.de/media/synthesis/200708/lookinside/thumbnails/10.1055-s-2007-966002-1.jpg"></a> <figcaption></figcaption> </figure> <h3 class="LVL2"> <EM CLASS="BOLD">Abstract</EM> </h3> <P>The catalytic addition of water to alkynes (hydration) generates valuable carbonyl compounds from unsaturated hydrocarbon precursors. Traditional mercury(II) catalysts hydrate terminal alkynes with Markovnikov selectivity to methyl ketones. Much research has been devoted to finding catalysts based on less toxic metals, the most promising being gold(I), gold(III), platinum(II), and palladium(II). Catalytic anti-Markovnikov hydration of terminal alkynes to aldehydes has been realized in an efficient manner with ruthenium(II) complex catalysts. The present review article lists known hydration catalysts and discusses applications of catalytic hydration to different classes of substrates, with an emphasis on functional group tolerance and regioselectivity.</P> <UL CLASS="UNNUMBERED"> <LI> <P>1 Introduction</P> </LI> <LI> <P>2 Timeline</P> </LI> <LI> <P>3 Alkyne Hydration Catalysts</P> </LI> <LI> <P>3.1 Brønsted Acid and Base Catalysts</P> </LI> <LI> <P>3.2 Mercury Catalysts</P> </LI> <LI> <P>3.3 Non-Mercurial Catalysts for Alkyne Hydration</P> </LI> <LI> <P>3.4 Anti-Markovnikov Hydration of Terminal Alkynes</P> </LI> <LI> <P>3.5 Enzymatic Hydration of Alkynes</P> </LI> <LI> <P>4 Mechanisms of Catalytic Alkyne Hydration</P> </LI> <LI> <P>4.1 Brønsted Acid Catalyzed Hydration</P> </LI> <LI> <P>4.2 Mercury-Catalyzed Hydration</P> </LI> <LI> <P>4.3 Other-Metal-Catalyzed Markovnikov Hydrations</P> </LI> <LI> <P>4.4 Mechanism of Ruthenium-Catalyzed Anti-Markovnikov Hydration</P> </LI> <LI> <P>5 Substrate Spectrum and Selectivity of Catalytic Alkyne Hydration</P> </LI> <LI> <P>5.1 Markovnikov Hydration Catalysis</P> </LI> <LI> <P>5.2 Anti-Markovnikov Hydration Catalysts</P> </LI> <LI> <P>6 Reactions Related to Catalytic Alkyne Hydration</P> </LI> <LI> <P>7 Conclusions and Outlook</P> </LI> </UL> <div class="articleKeywords"> <h3 class="LVL2"> <EM CLASS="BOLD">Key words</EM> </h3> <P>alkynes - catalysis - hydration - ketones - aldehydes</P> </div> </section> <section id="htmlfulltext"></section> <section id="references"> <ul class="literaturliste"> <h3 class="LVL2">References</h3> <li><A NAME="RE17407SS-1"><B>1</B></A> Classification according to: <SN>Jones</SN> RAY. <SN>Bunnett</SN> JF. 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Zani, L.; Hintermann, L. <EM CLASS="ITALIC">manuscript in preparation</EM>.</P><A NAME="RE17407SS-274"><B>274</B></A> <P>The price of 1 g of AuMe(PPh<sub>3</sub>) corresponds to that of 1 kg of mercury(II) sulfate!</P> </section> <section id="images"></section> <section id="supmat"> <ul class="tabBar borderBottom" id="supmatTabs"></ul> <div class="tabContentContainer"></div> </section> </div>  </article> <div class="metrics-container-main"> <div class="metrics-container-left"> <div class="metrics-container-cell"> <div class="metrics-altmetrics"><div data-doi="10.1055/s-2007-966002" class="altmetric-embed" data-link-target="_blank" data-badge-details="right" data-badge-type="donut" data-hide-no-mentions="true" ></div></div> </div> </div> <div class="metrics-container-right"> <div class="metrics-container-cell">  <div id="crossrefcites" class="crossrefcites" data-doi="10.1055/s-2007-966002"/></div> </div> </div> </div>  <div id="adSidebarOverBottom"> <script type="text/javascript"> window.TCFUtility.writeScript([ 'https://adfarm1.adition.com/js?wp_id=4863507&gdpr=${GDPR}&gdpr_consent=${GDPR_CONSENT_39}&prf[DOI]=10.1055-s-00000084&prf[UserLogin]=false&prf[IPLogin]=false&prf[MASTERKEY]=10.1055-s-00000084, false, false&prf[HWG]=false' ]); 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} let newLabel = document.createElement("label"); if (i == 0) { newLabel.style = "font-weight: bold" } var text = "Physician"; if (options[i] == 'Pflegekraft') { text = "Health and care worker"; } else if (options[i] == 'Therapeut') { text = "Therapist"; } else if (options[i] == 'Hebamme') { text = "Midwife/delivery nurse"; } else if (options[i] == 'Student') { text = "Student (human medicine, dentistry, veterinary medicine)"; } else if (options[i] == 'SonstigesSelect') { text = " "; } newLabel.innerHTML = " " + text; parentDiv.appendChild(newDiv); parentDiv.appendChild(newLabel); let selectList = document.createElement("select"); selectList.id = "doctorSelect"; selectList.setAttribute("onfocus", "this.size=10;"); selectList.setAttribute("onblur", "this.size=0;"); selectList.setAttribute("onchange", "this.size=1; this.blur();"); //selectList.name = "doctorSelect"; if (options[i] == 'SonstigesSelect') { for (let j = 0; j < selectOptions.length; j++) { var option = document.createElement("option"); if (selectOptions[j] == 'SonstigesSelect') { option.value = ""; } else { option.value = selectOptions[j]; } //option.setAttribute("class", "b"); var text = "other, please select"; if (selectOptions[j] == 'Apotheker') { text = "Pharmacist"; } else if (selectOptions[j] == 'Chemiker') { text = "Chemist"; } else if (selectOptions[j] == 'Pharmaunternehmen') { text = "Employee of pharmaceutical company / wholesaler"; } else if (selectOptions[j] == 'Assistenz') { text = "Medical technical assistant"; } else if (selectOptions[j] == 'Fachangestellter') { text = "Med. Medical Assistant"; } else if (selectOptions[j] == 'Rettungssanitaeter') { text = "Paramedic"; } else if (selectOptions[j] == 'Verwaltungsdienst') { text = "Administrative service in hospital"; } else if (selectOptions[j] == 'Wirtschaftsdienst') { text = "Economic and supply service in the hospital"; } else if (selectOptions[j] == 'TechnischerDienst') { text = "Technical service in the hospital"; } else if (selectOptions[j] == 'Sonstiges') { text = "Other"; } option.text = text; selectList.appendChild(option); } } if (selectList.length > 0) { parentDiv.appendChild(selectList); } document.getElementById("doctorFeedbackBlock").appendChild(parentDiv); } } }; $('#doctorFeedbackBlock').on('click', '.doctor-feedback-value', function() { var job = $('input[name="doctorRadio"]:checked').val(); if (job !== undefined && job.length > 0) { $('#doctorSelect').val(''); } }); //$('#doctorFeedbackBlock').on('change', '.doctorFeedbackElement', function() { // $('input[name="doctorRadio"]').filter('[value=""]').prop('checked', true); 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}); that.className += " feedback-selected" selectedFeedback = parseInt(this.getAttribute('data-value')); }); $("#hwgOk").click(function() { var hwgSubmit = $("#hgwSubmit").val(); // Feedback "Zufriedenheit" if (hwgSubmit === 'true') { if (selectedFeedback >= 0 && selectedFeedback < 11) { $("#hgwSubmit").val('false'); // send request const begrundung = $("#begrundung").val(); const url = '/products/json/addHwgValue?value=' + selectedFeedback + '&text=' + begrundung; const request = $.ajax({ type : 'GET', async : true, cache: false, url, success : function(data) { // close popup setCookie('hwg_value', false); $('#hwg-popover').css('display', 'none'); $("#begrundung").val(""); } }); } } }); $("#hwgCloseLink").click(function() { var hwgSubmit = $("#hgwSubmit").val(); $("#hgwSubmit").val('false'); if (hwgSubmit === 'true') { // send request const url = '/products/json/addHwgValue?value=keine Angabe&text='; const request = $.ajax({ type : 'GET', async : true, cache: false, url, success : function(data) { // close popup setCookie('hwg_value', false); $('#hwg-popover').css('display', 'none'); $("#begrundung").val(""); } }); } }); $("#hwgDoctorOk").click(function() { // send request var job = $('input[name="doctorRadio"]:checked').val() if (job == undefined || job.length == 0) { job = $('#doctorSelect').val(); } if (job !== undefined && job.length > 0) { //if($('input[name="doctorRadio"]:checked').val() === "Sonstiges") { if(job === "Arzt" || $('#doctorSelect').val() === "Apotheker" || $('#doctorSelect').val() === "Pharmaunternehmen") { setCookie('hwg_job_value', true); } else { setCookie('hwg_job_value', false); } $('#hwg-popover').css('display', 'none'); // TC-2224: Store profession const url = '/products/json/addHwgValue?value=profession&text=' + job; const request = $.ajax({ type : 'GET', async : true, cache: false, url, success : function(data) { // close popup $('#hwg-popover').css('display', 'none'); $("#begrundung").val(""); } }); } window.location.reload(); }); $("#doctorCloseLink").click(function() { // send request setCookie('hwg_job_value', false); 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