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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Coupling reaction</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. 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mw-list-item"><a href="https://ca.wikipedia.org/wiki/Reacci%C3%B3_d%27acoblament" title="Reacció d'acoblament – Catalan" lang="ca" hreflang="ca" data-title="Reacció d'acoblament" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/P%C3%A1rovac%C3%AD_reakce" title="Párovací reakce – Czech" lang="cs" hreflang="cs" data-title="Párovací reakce" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Koblingsreaktion" title="Koblingsreaktion – Danish" lang="da" hreflang="da" data-title="Koblingsreaktion" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Kupplungsreaktion" title="Kupplungsreaktion – German" lang="de" hreflang="de" data-title="Kupplungsreaktion" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Sidestusreaktsioon" title="Sidestusreaktsioon – Estonian" lang="et" hreflang="et" data-title="Sidestusreaktsioon" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Reacci%C3%B3n_de_acoplamiento" title="Reacción de acoplamiento – Spanish" lang="es" hreflang="es" data-title="Reacción de acoplamiento" 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/%D9%88%D8%A7%DA%A9%D9%86%D8%B4_%D8%AC%D9%81%D8%AA%E2%80%8C%D8%B4%D8%AF%D9%86" title="واکنش جفت‌شدن – Persian" lang="fa" hreflang="fa" data-title="واکنش جفت‌شدن" 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/R%C3%A9action_de_couplage" title="Réaction de couplage – French" lang="fr" hreflang="fr" data-title="Réaction de couplage" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Reaksi_penggandengan" title="Reaksi penggandengan – Indonesian" lang="id" hreflang="id" data-title="Reaksi 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href="https://nl.wikipedia.org/wiki/Koppelingsreactie" title="Koppelingsreactie – Dutch" lang="nl" hreflang="nl" data-title="Koppelingsreactie" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%AB%E3%83%83%E3%83%97%E3%83%AA%E3%83%B3%E3%82%B0%E5%8F%8D%E5%BF%9C" title="カップリング反応 – Japanese" lang="ja" hreflang="ja" data-title="カップリング反応" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Reakcja_sprz%C4%99gania" title="Reakcja sprzęgania – Polish" lang="pl" hreflang="pl" data-title="Reakcja sprzęgania" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Rea%C3%A7%C3%A3o_de_acoplamento" title="Reação de acoplamento – Portuguese" lang="pt" hreflang="pt" data-title="Reação de acoplamento" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Reac%C8%9Bie_de_cuplare" title="Reacție de cuplare – Romanian" lang="ro" hreflang="ro" data-title="Reacție de cuplare" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A0%D0%B5%D0%B0%D0%BA%D1%86%D0%B8%D0%B8_%D1%81%D0%BE%D1%87%D0%B5%D1%82%D0%B0%D0%BD%D0%B8%D1%8F" title="Реакции сочетания – Russian" lang="ru" hreflang="ru" data-title="Реакции сочетания" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Reakcije_spajanja" title="Reakcije spajanja – Slovenian" lang="sl" hreflang="sl" data-title="Reakcije spajanja" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Reakcije_pripajanja" title="Reakcije pripajanja – Serbian" lang="sr" hreflang="sr" data-title="Reakcije pripajanja" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a 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</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">Type of reaction in organic chemistry</div> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, a <b>coupling reaction</b> is a type of reaction in which two reactant molecules are bonded together. Such reactions often require the aid of a metal <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a>. In one important reaction type, a main group <a href="/wiki/Organometallic_compound" class="mw-redirect" title="Organometallic compound">organometallic compound</a> of the type R-M (where R = organic group, M = main group centre metal atom) reacts with an organic halide of the type R'-X with formation of a new <a href="/wiki/Carbon-carbon_bond" class="mw-redirect" title="Carbon-carbon bond">carbon-carbon bond</a> in the product R-R'. The most common type of coupling reaction is the <a href="/wiki/Cross_coupling_reaction" class="mw-redirect" title="Cross coupling reaction">cross coupling reaction</a>.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Pharma_3-0" class="reference"><a href="#cite_note-Pharma-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Richard_F._Heck" title="Richard F. Heck">Richard F. Heck</a>, <a href="/wiki/Ei-ichi_Negishi" title="Ei-ichi Negishi">Ei-ichi Negishi</a>, and <a href="/wiki/Akira_Suzuki_(chemist)" class="mw-redirect" title="Akira Suzuki (chemist)">Akira Suzuki</a> were awarded the 2010 <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize in Chemistry</a> for developing <a href="/wiki/Palladium-catalyzed_coupling_reactions" class="mw-redirect" title="Palladium-catalyzed coupling reactions">palladium-catalyzed cross coupling reactions</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><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> </p><p>Broadly speaking, two types of coupling reactions are recognized: </p> <ul><li>Homocouplings joining two identical partners. The product is symmetrical <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">R−R</span></li> <li>Heterocouplings joining two different <a href="/wiki/Cross-coupling_partner" title="Cross-coupling partner">partners</a>. These reactions are also called <a href="/wiki/Cross-coupling_reaction" title="Cross-coupling reaction">cross-coupling reactions</a>.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> The product is unsymmetrical, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−R'</span>.</li></ul> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Homo-coupling_types">Homo-coupling types</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Coupling_reaction&action=edit&section=1" title="Edit section: Homo-coupling types"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Coupling reactions are illustrated by the Ullmann reaction: </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Ullmann_reaction.svg" class="mw-file-description" title="Ullmann overview"><img alt="Ullmann overview" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b1/Ullmann_reaction.svg/350px-Ullmann_reaction.svg.png" decoding="async" width="350" height="81" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b1/Ullmann_reaction.svg/525px-Ullmann_reaction.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b1/Ullmann_reaction.svg/700px-Ullmann_reaction.svg.png 2x" data-file-width="650" data-file-height="150" /></a><figcaption>Ullmann overview</figcaption></figure> <table align="center" class="wikitable"> <tbody><tr> <th>Reaction</th> <th>Year </th> <th colspan="2" align="left">Organic compound</th> <th>Coupler</th> <th>Remark </th></tr> <tr> <td><a href="/wiki/Wurtz_reaction" title="Wurtz reaction">Wurtz reaction</a></td> <td>1855</td> <td>R-X</td> <td>sp<sup>3</sup></td> <td>Na as reductant</td> <td>dry ether as medium </td></tr> <tr> <td><a href="/wiki/Pinacol_coupling_reaction" title="Pinacol coupling reaction">Pinacol coupling reaction</a></td> <td>1859</td> <td>R-HC=O or R<sub>2</sub>(C=O)</td> <td></td> <td>various metals</td> <td>requires proton donor </td></tr> <tr> <td><a href="/wiki/Glaser_coupling" title="Glaser coupling">Glaser coupling</a></td> <td>1869</td> <td>RC≡CH</td> <td>sp</td> <td>Cu</td> <td>O<sub>2</sub> as H-acceptor </td></tr> <tr> <td><a href="/wiki/Ullmann_reaction" title="Ullmann reaction">Ullmann reaction</a></td> <td>1901</td> <td>Ar-X</td> <td>sp<sup>2</sup></td> <td>Cu</td> <td>high temperatures </td></tr> <tr> <td><a href="/wiki/Wurtz%E2%80%93Fittig_reaction" title="Wurtz–Fittig reaction">Fittig reaction</a></td> <td></td> <td>Ar-X</td> <td>sp<sup>2</sup></td> <td>Na</td> <td>dry ether as medium </td></tr> <tr> <td><a href="/wiki/Scholl_reaction" title="Scholl reaction">Scholl reaction</a></td> <td>1910</td> <td>ArH</td> <td>sp<sup>2</sup></td> <td>NaAlCl<sub>4</sub>(<i>l</i>)</td> <td>O<sub>2</sub> as H-acceptor; presumably trace Fe<sup>3+</sup> catalyst; requires high heat </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Cross-coupling_types">Cross-coupling types</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Coupling_reaction&action=edit&section=2" title="Edit section: Cross-coupling types"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Cross-coupling_reaction" title="Cross-coupling reaction">Cross-coupling reaction</a></div> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Heck_Reaction_Scheme.png" class="mw-file-description" title="The Heck reaction"><img alt="The Heck reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Heck_Reaction_Scheme.png/300px-Heck_Reaction_Scheme.png" decoding="async" width="300" height="67" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Heck_Reaction_Scheme.png/450px-Heck_Reaction_Scheme.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Heck_Reaction_Scheme.png/600px-Heck_Reaction_Scheme.png 2x" data-file-width="984" data-file-height="219" /></a><figcaption>The Heck reaction</figcaption></figure> <table align="center" class="wikitable"> <tbody><tr> <th>Reaction</th> <th>Year </th> <th colspan="2" align="left">Reactant A </th> <th colspan="2" align="left">Reactant B</th> <th>Catalyst</th> <th>Remark </th></tr> <tr> <td><a href="/wiki/Grignard_reaction" title="Grignard reaction">Grignard reaction</a></td> <td>1900</td> <td>R-MgBr</td> <td>sp, sp<sup>2</sup>, sp<sup>3</sup> </td> <td>R-HC=O or R(C=O)R<sub>2</sub></td> <td>sp<sup>2</sup></td> <td>not catalytic </td></tr> <tr> <td><a href="/wiki/Gomberg-Bachmann_reaction" class="mw-redirect" title="Gomberg-Bachmann reaction">Gomberg-Bachmann reaction</a> </td> <td>1924 </td> <td>Ar-H </td> <td>sp<sup>2</sup> </td> <td>Ar'-N<sub>2</sub><sup>+</sup>X<sup>−</sup> </td> <td>sp<sup>2</sup> </td> <td>not catalytic </td></tr> <tr> <td><a href="/wiki/Cadiot-Chodkiewicz_coupling" class="mw-redirect" title="Cadiot-Chodkiewicz coupling">Cadiot-Chodkiewicz coupling</a></td> <td>1957</td> <td>RC≡CH</td> <td>sp</td> <td>RC≡CX</td> <td>sp</td> <td>Cu</td> <td>requires base </td></tr> <tr> <td><a href="/wiki/Castro-Stephens_coupling" class="mw-redirect" title="Castro-Stephens coupling">Castro-Stephens coupling</a></td> <td>1963</td> <td>RC≡CH</td> <td>sp</td> <td>Ar-X</td> <td>sp<sup>2</sup></td> <td>Cu</td> <td> </td></tr> <tr> <td><a href="/wiki/Corey-House_synthesis" class="mw-redirect" title="Corey-House synthesis">Corey-House synthesis</a></td> <td>1967</td> <td>R<sub>2</sub>CuLi or RMgX</td> <td>sp<sup>3</sup> </td> <td>R-X</td> <td>sp<sup>2</sup>, sp<sup>3</sup> </td> <td>Cu </td> <td>Cu-catalyzed version by Kochi, 1971 </td></tr> <tr> <td><a href="/w/index.php?title=Cassar_reaction&action=edit&redlink=1" class="new" title="Cassar reaction (page does not exist)">Cassar reaction</a></td> <td>1970</td> <td>Alkene</td> <td>sp<sup>2</sup></td> <td>R-X</td> <td>sp<sup>3</sup></td> <td>Pd</td> <td>requires base </td></tr> <tr> <td><a href="/wiki/Kumada_coupling" title="Kumada coupling">Kumada coupling</a></td> <td>1972</td> <td>Ar-MgBr</td> <td>sp<sup>2</sup>, sp<sup>3</sup></td> <td>Ar-X</td> <td>sp<sup>2</sup></td> <td>Pd or Ni or Fe</td> <td> </td></tr> <tr> <td><a href="/wiki/Heck_reaction" title="Heck reaction">Heck reaction</a></td> <td>1972</td> <td>alkene</td> <td>sp<sup>2</sup></td> <td>Ar-X</td> <td>sp<sup>2</sup></td> <td>Pd or Ni</td> <td>requires base </td></tr> <tr> <td><a href="/wiki/Sonogashira_coupling" title="Sonogashira coupling">Sonogashira coupling</a></td> <td>1975</td> <td>RC≡CH</td> <td>sp</td> <td>R-X</td> <td>sp<sup>3</sup> sp<sup>2</sup></td> <td>Pd and Cu</td> <td>requires base </td></tr> <tr> <td>Murahashi coupling<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td> <td>1975 </td> <td>RLi </td> <td>sp<sup>2</sup>, sp<sup>3</sup> </td> <td>Ar-X </td> <td>sp<sup>2</sup> </td> <td>Pd or Ni </td> <td>Pd-catalyzed version by Murahashi, 1979 </td></tr> <tr> <td><a href="/wiki/Negishi_coupling" title="Negishi coupling">Negishi coupling</a></td> <td>1977</td> <td>R-Zn-X</td> <td>sp<sup>3</sup>, sp<sup>2</sup>, sp</td> <td>R-X</td> <td>sp<sup>3</sup> sp<sup>2</sup></td> <td>Pd or Ni</td> <td> </td></tr> <tr> <td><a href="/wiki/Stille_cross_coupling" class="mw-redirect" title="Stille cross coupling">Stille cross coupling</a></td> <td>1978</td> <td>R-SnR<sub>3</sub></td> <td>sp<sup>3</sup>, sp<sup>2</sup>, sp</td> <td>R-X</td> <td>sp<sup>3</sup> sp<sup>2</sup></td> <td>Pd</td> <td> </td></tr> <tr> <td><a href="/wiki/Suzuki_reaction" title="Suzuki reaction">Suzuki reaction</a></td> <td>1979</td> <td>R-B(OR)<sub>2</sub></td> <td>sp<sup>2</sup></td> <td>R-X</td> <td>sp<sup>3</sup> sp<sup>2</sup></td> <td>Pd or Ni</td> <td>requires base </td></tr> <tr> <td><a href="/wiki/Hiyama_coupling" title="Hiyama coupling">Hiyama coupling</a></td> <td>1988</td> <td>R-SiR<sub>3</sub></td> <td>sp<sup>2</sup></td> <td>R-X</td> <td>sp<sup>3</sup> sp<sup>2</sup></td> <td>Pd</td> <td>requires base </td></tr> <tr> <td><a href="/wiki/Buchwald-Hartwig_reaction" class="mw-redirect" title="Buchwald-Hartwig reaction">Buchwald-Hartwig reaction</a></td> <td>1994</td> <td>R<sub>2</sub>N-H</td> <td>sp<sup>3</sup></td> <td>R-X</td> <td>sp<sup>2</sup></td> <td>Pd</td> <td>N-C coupling,<br />second generation free amine </td></tr> <tr> <td><a href="/wiki/Fukuyama_coupling" title="Fukuyama coupling">Fukuyama coupling</a></td> <td>1998</td> <td>R-Zn-I</td> <td>sp<sup>3</sup></td> <td>RCO(SEt)</td> <td>sp<sup>2</sup></td> <td>Pd or Ni<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></td> <td> </td></tr> <tr> <td><a href="/wiki/Liebeskind%E2%80%93Srogl_coupling" title="Liebeskind–Srogl coupling">Liebeskind–Srogl coupling</a></td> <td>2000</td> <td>R-B(OR)<sub>2</sub></td> <td>sp<sup>3</sup>, sp<sup>2</sup></td> <td>RCO(SEt) Ar-SMe</td> <td>sp<sup>2</sup></td> <td>Pd</td> <td>requires <a href="/wiki/CuTC" class="mw-redirect" title="CuTC">CuTC</a> </td></tr> <tr> <td>(Li) <a href="/wiki/Cross_dehydrogenative_coupling" title="Cross dehydrogenative coupling">Cross dehydrogenative coupling</a>(CDC)</td> <td>2004</td> <td>R-H</td> <td>sp, sp<sup>2</sup>, sp<sup>3</sup></td> <td>R'-H</td> <td>sp, sp<sup>2</sup>, sp<sup>3</sup></td> <td>Cu, Fe, Pd etc</td> <td>requires oxidant or dehydrogenation </td></tr> <tr> <td><a href="/wiki/Wurtz%E2%80%93Fittig_reaction" title="Wurtz–Fittig reaction">Wurtz-Fittig reaction</a> </td> <td> </td> <td>R-X </td> <td>sp<sup>3</sup> </td> <td>Ar-X </td> <td>sp<sup>2</sup> </td> <td>Na </td> <td>dry ether </td></tr></tbody></table> <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=Coupling_reaction&action=edit&section=3" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Coupling reactions are routinely employed in the preparation of pharmaceuticals.<sup id="cite_ref-Pharma_3-1" class="reference"><a href="#cite_note-Pharma-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Conjugated polymers are prepared using this technology as well.<sup id="cite_ref-JFH_9-0" class="reference"><a href="#cite_note-JFH-9"><span class="cite-bracket">[</span>9<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=Coupling_reaction&action=edit&section=4" 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 reflist-columns references-column-width reflist-columns-2"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><i>Organic Synthesis using Transition Metals</i> Rod Bates <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><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-84127-107-1" title="Special:BookSources/978-1-84127-107-1">978-1-84127-107-1</a></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><i>New Trends in Cross-Coupling: Theory and Applications</i> Thomas Colacot (Editor) 2014 <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/978-1-84973-896-5" title="Special:BookSources/978-1-84973-896-5">978-1-84973-896-5</a></span> </li> <li id="cite_note-Pharma-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Pharma_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Pharma_3-1"><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="CITEREFKing,_A._O.Yasuda,_N.2004" class="citation book cs1">King, A. O.; Yasuda, N. (2004). "Palladium-Catalyzed Cross-Coupling Reactions in the Synthesis of Pharmaceuticals". <i>Organometallics in Process Chemistry</i>. Topics in Organometallic Chemistry. Vol. 6. Heidelberg: Springer. pp. 205–245. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fb94551">10.1007/b94551</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-540-01603-8" title="Special:BookSources/978-3-540-01603-8"><bdi>978-3-540-01603-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Palladium-Catalyzed+Cross-Coupling+Reactions+in+the+Synthesis+of+Pharmaceuticals&rft.btitle=Organometallics+in+Process+Chemistry&rft.place=Heidelberg&rft.series=Topics+in+Organometallic+Chemistry&rft.pages=205-245&rft.pub=Springer&rft.date=2004&rft_id=info%3Adoi%2F10.1007%2Fb94551&rft.isbn=978-3-540-01603-8&rft.au=King%2C+A.+O.&rft.au=Yasuda%2C+N.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACoupling+reaction" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://nobelprize.org/nobel_prizes/pornhemistry/laureates/2010/">"The Nobel Prize in Chemistry 2010 - Richard F. Heck, Ei-ichi Negishi, Akira Suzuki"</a>. NobelPrize.org. 2010-10-06<span class="reference-accessdate">. Retrieved <span class="nowrap">2010-10-06</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=The+Nobel+Prize+in+Chemistry+2010+-+Richard+F.+Heck%2C+Ei-ichi+Negishi%2C+Akira+Suzuki&rft.pub=NobelPrize.org&rft.date=2010-10-06&rft_id=http%3A%2F%2Fnobelprize.org%2Fnobel_prizes%2Fpornhemistry%2Flaureates%2F2010%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACoupling+reaction" class="Z3988"></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="CITEREFJohansson_SeechurnKitchingColacotSnieckus2012" class="citation journal cs1">Johansson Seechurn, Carin C. C.; Kitching, Matthew O.; Colacot, Thomas J.; Snieckus, Victor (2012). "Palladium-Catalyzed Cross-Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize". <i>Angewandte Chemie International Edition</i>. <b>51</b> (21): 5062–5085. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.201107017">10.1002/anie.201107017</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/22573393">22573393</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angewandte+Chemie+International+Edition&rft.atitle=Palladium-Catalyzed+Cross-Coupling%3A+A+Historical+Contextual+Perspective+to+the+2010+Nobel+Prize&rft.volume=51&rft.issue=21&rft.pages=5062-5085&rft.date=2012&rft_id=info%3Adoi%2F10.1002%2Fanie.201107017&rft_id=info%3Apmid%2F22573393&rft.aulast=Johansson+Seechurn&rft.aufirst=Carin+C.+C.&rft.au=Kitching%2C+Matthew+O.&rft.au=Colacot%2C+Thomas+J.&rft.au=Snieckus%2C+Victor&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACoupling+reaction" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSmith,_Michael_B.March,_Jerry2007" class="citation cs2">Smith, Michael B.; <a href="/wiki/Jerry_March" title="Jerry March">March, Jerry</a> (2007), <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JDR-nZpojeEC&printsec=frontcover"><i>Advanced Organic Chemistry: Reactions, Mechanisms, and Structure</i></a> (6th ed.), New York: Wiley-Interscience, p. 449, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-72091-1" title="Special:BookSources/978-0-471-72091-1"><bdi>978-0-471-72091-1</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry%3A+Reactions%2C+Mechanisms%2C+and+Structure&rft.place=New+York&rft.pages=449&rft.edition=6th&rft.pub=Wiley-Interscience&rft.date=2007&rft.isbn=978-0-471-72091-1&rft.au=Smith%2C+Michael+B.&rft.au=March%2C+Jerry&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJDR-nZpojeEC%26printsec%3Dfrontcover&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACoupling+reaction" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHazraJohansson_SeechurnHandaColacot2021" class="citation journal cs1">Hazra, Susanta; Johansson Seechurn, Carin C. 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"Directed Nickel-Catalyzed Negishi Cross Coupling of Alkyl Aziridines". <i>Journal of the American Chemical Society</i>. <b>135</b> (36): 13605–13609. <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%2Fja4076716">10.1021/ja4076716</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0002-7863">0002-7863</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/23961769">23961769</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=Directed+Nickel-Catalyzed+Negishi+Cross+Coupling+of+Alkyl+Aziridines&rft.volume=135&rft.issue=36&rft.pages=13605-13609&rft.date=2013-08-20&rft.issn=0002-7863&rft_id=info%3Apmid%2F23961769&rft_id=info%3Adoi%2F10.1021%2Fja4076716&rft.aulast=Nielsen&rft.aufirst=Daniel+K.&rft.au=Huang%2C+Chung-Yang+%28Dennis%29&rft.au=Doyle%2C+Abigail+G.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACoupling+reaction" class="Z3988"></span></span> </li> <li id="cite_note-JFH-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-JFH_9-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHartwig,_J._F.2010" class="citation book cs1">Hartwig, J. F. (2010). <i>Organotransition Metal Chemistry, from Bonding to Catalysis</i>. New York: University Science Books. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-891389-53-5" title="Special:BookSources/978-1-891389-53-5"><bdi>978-1-891389-53-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organotransition+Metal+Chemistry%2C+from+Bonding+to+Catalysis&rft.place=New+York&rft.pub=University+Science+Books&rft.date=2010&rft.isbn=978-1-891389-53-5&rft.au=Hartwig%2C+J.+F.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACoupling+reaction" class="Z3988"></span></span> </li> </ol></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output 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