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href="/wiki/C-H_bond" class="mw-redirect" title="C-H bond">C-H bond</a> of <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> (<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">H<sub class="template-chem2-sub">2</sub>C=CH<sub class="template-chem2-sub">2</sub></span>): </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">2</sub>=CHR + CH<sub class="template-chem2-sub">2</sub>=CH<sub class="template-chem2-sub">2</sub> → CH<sub class="template-chem2-sub">3</sub>−CHR−CH=CH<sub class="template-chem2-sub">2</sub></span></dd></dl> <p>The more general reaction, <b>hydroalkenylation</b>, is the formal insertion of an alkene into the C-H bond of any <a href="/wiki/Terminal_alkene" title="Terminal alkene">terminal alkene</a>. The reaction is catalyzed by <a href="/wiki/Metal_complex" class="mw-redirect" title="Metal complex">metal complexes</a>. A representative reaction is the conversion of <a href="/wiki/Styrene" title="Styrene">styrene</a> and ethylene to 3-phenybutene:<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> </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {PhCH=CH2}}+{\color {red}{\ce {CH2=CH2}}}\longrightarrow {\color {red}{\ce {H -}}}{\ce {CH2-CH(Ph)}}{\color {red}{\ce {-CH=CH2}}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>PhCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> <mo>+</mo> <mrow class="MJX-TeXAtom-ORD"> <mstyle mathcolor="red"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <mo stretchy="false">⟶</mo> <mrow class="MJX-TeXAtom-ORD"> <mstyle mathcolor="red"> <mrow class="MJX-TeXAtom-ORD"> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> </mrow> </mstyle> </mrow> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>Ph</mtext> <mo stretchy="false">)</mo> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mstyle mathcolor="red"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {PhCH=CH2}}+{\color {red}{\ce {CH2=CH2}}}\longrightarrow {\color {red}{\ce {H -}}}{\ce {CH2-CH(Ph)}}{\color {red}{\ce {-CH=CH2}}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/2c9cba49fdd617d40e538c1fd4ab48e4f1a28560" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:60.729ex; height:3.009ex;" alt="{\displaystyle {\ce {PhCH=CH2}}+{\color {red}{\ce {CH2=CH2}}}\longrightarrow {\color {red}{\ce {H -}}}{\ce {CH2-CH(Ph)}}{\color {red}{\ce {-CH=CH2}}}}"></span></dd></dl> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Ethylene_dimerization">Ethylene dimerization</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrovinylation&action=edit&section=1" title="Edit section: Ethylene dimerization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Dimerization" title="Dimerization">dimerization</a> of ethylene which gives <a href="/wiki/1-butene" class="mw-redirect" title="1-butene">1-butene</a> is another example of a hydrovinylation. In the <b>Dimersol</b> and <b>Alphabutol</b> Processes, alkenes are dimerized for the production of gasoline and for comonomers such as 1-butene. These processes operate at several refineries across the world at the scales of about 400,000 tons/year (2006 report).<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> 1-Butene is amenable to isomerization to <a href="/wiki/But-2-ene" title="But-2-ene">2-butenes</a>, which is used in <a href="/wiki/Olefin_conversion_technology" title="Olefin conversion technology">olefin conversion technology</a> to give <a href="/wiki/Propylene" title="Propylene">propylene</a>. </p> <div class="mw-heading mw-heading2"><h2 id="In_organic_synthesis">In organic synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrovinylation&action=edit&section=2" title="Edit section: In organic synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The addition can be done highly regio- and stereoselectively, although the choices of metal, ligands, and counterions often play very important role. Many metals have also been demonstrated to form active catalysts, including nickel<sup id="cite_ref-Ho2010_3-0" class="reference"><a href="#cite_note-Ho2010-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ho2012_4-0" class="reference"><a href="#cite_note-Ho2012-4"><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> and cobalt.<sup id="cite_ref-Vogt2006_6-0" class="reference"><a href="#cite_note-Vogt2006-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Hilt2009_7-0" class="reference"><a href="#cite_note-Hilt2009-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-RajanBabu2010_8-0" class="reference"><a href="#cite_note-RajanBabu2010-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>In a stoichiometric version of a hydrovinylation reaction, nucleophiles add to an electrophilic <a href="/wiki/Transition_metal_alkene_complex" title="Transition metal alkene complex">transition metal alkene complex</a>, forming a C-C bond. The resulting metal alkyl undergoes beta-hydride elimination, liberating the vinylated product.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Hydroarylation">Hydroarylation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrovinylation&action=edit&section=3" title="Edit section: Hydroarylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><b>Hydroarylation</b> is again a special case of hydrovinylation. Hydroarylation has been demonstrated for alkyne and alkene substrates. An early example was provided by the <a href="/wiki/Murai_reaction" title="Murai reaction">Murai reaction</a>, which involves the insertion of alkenes into a C-H bond of <a href="/wiki/Acetophenone" title="Acetophenone">acetophenone</a>. The keto group directs the regiochemistry, stabilizing an aryl intermediate.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Figure_1._General_scheme_of_a_Murai_reaction.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Figure_1._General_scheme_of_a_Murai_reaction.png/504px-Figure_1._General_scheme_of_a_Murai_reaction.png" decoding="async" width="504" height="114" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Figure_1._General_scheme_of_a_Murai_reaction.png/756px-Figure_1._General_scheme_of_a_Murai_reaction.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Figure_1._General_scheme_of_a_Murai_reaction.png/1008px-Figure_1._General_scheme_of_a_Murai_reaction.png 2x" data-file-width="1360" data-file-height="307" /></a><figcaption>A Murai reaction (X = directing group, typically X = O).</figcaption></figure> <p>When catalyzed by palladium carboxylates, a key step is <a href="/wiki/Electrophilic_aromatic_substitution" title="Electrophilic aromatic substitution">electrophilic aromatic substitution</a> to give a Pd(II) aryl intermediate.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Gold behaves similarly.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> <b>Hydropyridination</b> is a similar reaction, but entails addition of a pyridyl-H bond to alkenes and alkynes.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrovinylation&action=edit&section=4" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Vinylation" title="Vinylation">Vinylation</a>, the process of affixing a <a href="/wiki/Vinyl_group" title="Vinyl group">vinyl group</a></li></ul> <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=Hydrovinylation&action=edit&section=5" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-references-wrap mw-references-columns"><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"><style 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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="CITEREFT._V._RajanBabuG._A._Cox2014" class="citation encyclopaedia cs1">T. 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