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<span>CO insertion</span> </div> </a> <button aria-controls="toc-CO_insertion-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 CO insertion subsection</span> </button> <ul id="toc-CO_insertion-sublist" class="vector-toc-list"> <li id="toc-Effects_on_reaction_rates" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Effects_on_reaction_rates"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Effects on reaction rates</span> </div> </a> <ul id="toc-Effects_on_reaction_rates-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reverse_reaction" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reverse_reaction"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Reverse reaction</span> </div> </a> <ul id="toc-Reverse_reaction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Insertion_of_other_oxides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Insertion_of_other_oxides"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Insertion of other oxides</span> </div> </a> <ul id="toc-Insertion_of_other_oxides-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Insertion_of_alkenes_into_metal-carbon_bonds" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Insertion_of_alkenes_into_metal-carbon_bonds"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Insertion of alkenes into metal-carbon bonds</span> </div> </a> <button aria-controls="toc-Insertion_of_alkenes_into_metal-carbon_bonds-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 Insertion of alkenes into metal-carbon bonds subsection</span> </button> <ul id="toc-Insertion_of_alkenes_into_metal-carbon_bonds-sublist" class="vector-toc-list"> <li id="toc-Mechanism" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Mechanism"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Mechanism</span> </div> </a> <ul id="toc-Mechanism-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Insertion_of_alkenes_into_M–H_bonds" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Insertion_of_alkenes_into_M–H_bonds"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Insertion of alkenes into M–H bonds</span> </div> </a> <button aria-controls="toc-Insertion_of_alkenes_into_M–H_bonds-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon 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<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">Chemical reaction in which two ligands of a metal complex combine</div> <p>In <a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">organometallic chemistry</a>, a <b>migratory insertion</b> is a type of <a href="/wiki/Chemical_reaction" title="Chemical reaction">reaction</a> wherein two <a href="/wiki/Ligand" title="Ligand">ligands</a> on a <a href="/wiki/Metal_complex" class="mw-redirect" title="Metal complex">metal complex</a> combine. It is a subset of reactions that very closely resembles the <a href="/wiki/Insertion_reaction" title="Insertion reaction">insertion reactions</a>, and both are differentiated by the <a href="/wiki/Reaction_mechanism" title="Reaction mechanism">mechanism</a> that leads to the resulting <a href="/wiki/Stereochemistry" title="Stereochemistry">stereochemistry</a> of the products. However, often the two are used interchangeably because the mechanism is sometimes unknown. Therefore, migratory insertion reactions or insertion reactions, for short, are defined not by the mechanism but by the overall <a href="/wiki/Regiochemistry" class="mw-redirect" title="Regiochemistry">regiochemistry</a> wherein one chemical entity interposes itself into an existing <a href="/wiki/Chemical_bond" title="Chemical bond">bond</a> of typically a second chemical entity e.g.:<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 {\color {red}{\ce {A}}}+{\color {blue}{\ce {B-C}}}\longrightarrow {\color {blue}{\ce {B{-}}}}{\color {red}{\ce {A}}}{\color {blue}{\ce {-C}}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mstyle mathcolor="red"> <mrow class="MJX-TeXAtom-ORD"> <mtext>A</mtext> </mrow> </mstyle> </mrow> <mo>+</mo> <mrow class="MJX-TeXAtom-ORD"> <mstyle mathcolor="blue"> <mrow class="MJX-TeXAtom-ORD"> <mtext>B</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>C</mtext> </mrow> </mstyle> </mrow> <mo stretchy="false">⟶</mo> <mrow class="MJX-TeXAtom-ORD"> <mstyle mathcolor="blue"> <mrow class="MJX-TeXAtom-ORD"> <mtext>B</mtext> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> </mrow> </mrow> </mstyle> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mstyle mathcolor="red"> <mrow class="MJX-TeXAtom-ORD"> <mtext>A</mtext> </mrow> </mstyle> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mstyle mathcolor="blue"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>C</mtext> </mrow> </mstyle> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\color {red}{\ce {A}}}+{\color {blue}{\ce {B-C}}}\longrightarrow {\color {blue}{\ce {B{-}}}}{\color {red}{\ce {A}}}{\color {blue}{\ce {-C}}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/d10753c193fd6e2ecf556eb706033ec486ae160a" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:23.494ex; height:2.343ex;" alt="{\displaystyle {\color {red}{\ce {A}}}+{\color {blue}{\ce {B-C}}}\longrightarrow {\color {blue}{\ce {B{-}}}}{\color {red}{\ce {A}}}{\color {blue}{\ce {-C}}}}"></span></dd></dl> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Overview">Overview</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Migratory_insertion&action=edit&section=1" title="Edit section: Overview"><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">See also: <a href="/wiki/Ligand#Classification_of_ligands_as_L_and_X" title="Ligand">Ligand § Classification of ligands as L and X</a></div> <p>In the migratory insertion, a ligand that is viewed as an <a href="/wiki/Anion" class="mw-redirect" title="Anion">anion</a> (X) ligand in and a ligand that is viewed as <a href="/wiki/Neutral_particle" title="Neutral particle">neutral</a> couple, generating a new anionic ligand. The anion and neutral ligands that react are adjacent. If the <a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">precursor</a> complex is <a href="/wiki/Coordinatively_saturated" class="mw-redirect" title="Coordinatively saturated">coordinatively saturated</a>, migratory insertion often result in a <a href="/wiki/Coordinatively_unsaturated" class="mw-redirect" title="Coordinatively unsaturated">coordinatively unsaturated</a> product. A new (neutral) ligand can then react with the <a href="/wiki/Metal" title="Metal">metal</a> leading to a further insertion. The process can occur many times on a single metal, as in <a href="/wiki/Olefin_polymerization" class="mw-redirect" title="Olefin polymerization">olefin polymerization</a>. </p><p>The anionic ligand can be: H<sup>−</sup> (<a href="/wiki/Hydride" title="Hydride">hydride</a>), R<sup>−</sup> (alkyl), <a href="/wiki/Acyl" class="mw-redirect" title="Acyl">acyl</a>, Ar<sup>−</sup> (<a href="/wiki/Aryl" class="mw-redirect" title="Aryl">aryl</a>), or OR<sup>−</sup> (<a href="/wiki/Alkoxide" title="Alkoxide">alkoxide</a>). The ability of these groups to migrate is called their <a href="/wiki/Migratory_aptitude" title="Migratory aptitude">migratory aptitude</a>. The neutral ligand can be CO, <a href="/wiki/Alkene" title="Alkene">alkene</a>, <a href="/wiki/Alkyne" title="Alkyne">alkyne</a>, or in some cases, even <a href="/wiki/Carbene" title="Carbene">carbene</a>. </p><p>Diverse reactions apply to the migratory insertion. One mechanism involves the attack of the anionic ligand on the <a href="/wiki/Electrophile" title="Electrophile">electrophilic</a> part of the neutral ligand (the anionic ligand migrates to the neutral ligand). The other mechanism involves the neutral ligand inserts itself between the metal and the anionic ligand. </p> <div class="mw-heading mw-heading2"><h2 id="CO_insertion">CO insertion</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Migratory_insertion&action=edit&section=2" title="Edit section: CO insertion"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The insertion of <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> into a metal-carbon bond to form an <a href="/wiki/Acyl" class="mw-redirect" title="Acyl">acyl</a> group is the basis of <a href="/wiki/Carbonylation" title="Carbonylation">carbonylation</a> reactions, which provides many commercially useful products. Mechanistic studies reveal that the alkyl group migrates intramolecularly to an adjacent CO ligand.<sup id="cite_ref-Hartwig_2-0" class="reference"><a href="#cite_note-Hartwig-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Insertion_reaction_for_an_octahedral_complex.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Insertion_reaction_for_an_octahedral_complex.png/606px-Insertion_reaction_for_an_octahedral_complex.png" decoding="async" width="606" height="106" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Insertion_reaction_for_an_octahedral_complex.png/909px-Insertion_reaction_for_an_octahedral_complex.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/13/Insertion_reaction_for_an_octahedral_complex.png/1212px-Insertion_reaction_for_an_octahedral_complex.png 2x" data-file-width="2527" data-file-height="440" /></a><figcaption>CO Insertion reaction pathway for an octahedral complex</figcaption></figure></dd></dl> <p>Early studies were conducted on the conversion of <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">CH<sub class="template-chem2-sub">3</sub>Mn(CO)<sub class="template-chem2-sub">5</sub></span> to give the acetyl derivative.<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> Using <sup>13</sup>CO, the products is cis [Mn(COCH<sub>3</sub>)(<sup>13</sup>CO)(CO)<sub>4</sub>] (scheme 1). </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:CO_insertion.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9c/CO_insertion.png/364px-CO_insertion.png" decoding="async" width="364" height="135" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/9/9c/CO_insertion.png 1.5x" data-file-width="481" data-file-height="179" /></a><figcaption>Scheme 1. Note the solvent changing in the backward reaction: heptane is a high-boiling solvent, suitable for the temperature indicated.</figcaption></figure> <p>CO insertion does not always involve migration. Treatment of CpFe(L)(CO)CH<sub>3</sub> with <sup>13</sup>CO yields a mix of both alkyl migration products and products formed by true insertion of bound <a href="/wiki/Carbonyls" class="mw-redirect" title="Carbonyls">carbonyls</a> into the <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a> group. Product distribution is influenced by the choice of <a href="/wiki/Solvent" title="Solvent">solvent</a>.<sup id="cite_ref-ACR_5-0" class="reference"><a href="#cite_note-ACR-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Alkyl derivatives of <a href="/wiki/Square_planar_molecular_geometry" title="Square planar molecular geometry">square planar complexes</a> undergo CO insertions particularly readily. Insertion reactions on square planar complexes are of particular interest because of their industrial applications. Since square planar complexes are often <a href="/wiki/Coordinatively_unsaturated" class="mw-redirect" title="Coordinatively unsaturated">coordinatively unsaturated</a>, they are susceptible to formation of 5-coordinate adducts, which undergo migratory insertion readily.<sup id="cite_ref-ACR_5-1" class="reference"><a href="#cite_note-ACR-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> In most cases the in-plane migration pathway is preferred, but, unlike the <a href="/wiki/Nucleophilic" class="mw-redirect" title="Nucleophilic">nucleophilic</a> pathway, it is inhibited by an excess of CO.<sup id="cite_ref-CCR_6-0" class="reference"><a href="#cite_note-CCR-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Square_Planar.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Square_Planar.png/800px-Square_Planar.png" decoding="async" width="800" height="81" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/5/58/Square_Planar.png 1.5x" data-file-width="1021" data-file-height="104" /></a><figcaption>Nucleophilic insertion and rearrangement of a square planar complex</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Effects_on_reaction_rates">Effects on reaction rates</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Migratory_insertion&action=edit&section=3" title="Edit section: Effects on reaction rates"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Steric_effects" title="Steric effects">Steric effects</a> strain – Increasing the steric strain of the <a href="/wiki/Chelation" title="Chelation">chelate</a> backbone in square planar complexes pushes the carbonyl and methyl groups closer together, increasing the reactivity of insertion reactions.<sup id="cite_ref-CCR_6-1" class="reference"><a href="#cite_note-CCR-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Oxidation_state" title="Oxidation state">Oxidation state</a> – Oxidation of the metal tends to increase insertion reaction rates. The main rate-limiting step in the mechanism is the migration of the methyl group onto a carbonyl ligand, oxidizing the metal by imparting a greater partial positive charge on the acetyl carbon, and thus increasing the rate of reaction.<sup id="cite_ref-Brown_7-0" class="reference"><a href="#cite_note-Brown-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Lewis_acids_and_bases" title="Lewis acids and bases">Lewis acids</a> – Lewis acids also increase the reaction rates, for reasons similar to metal oxidation increasing the positive charge on the carbon. Lewis acids bind to the CO oxygen and remove charge, increasing the electrophilicity of the carbon. This can increase the reaction rate by a factor of up to 10<sup>8</sup>, and the complex formed is stable enough that the reaction proceeds even without additional CO to bind to the metal.<sup id="cite_ref-Brown_7-1" class="reference"><a href="#cite_note-Brown-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Electronegativity" title="Electronegativity">Electronegativity</a> of the <a href="/wiki/Leaving_group" title="Leaving group">leaving group</a> - Increasing the electronegativity of the leaving alkyl group stabilizes the metal-carbon bond interaction and thus increases the <a href="/wiki/Activation_energy" title="Activation energy">activation energy</a> required for migration, decreasing the reaction rate.<sup id="cite_ref-Shusterman_8-0" class="reference"><a href="#cite_note-Shusterman-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Trans_effect" title="Trans effect"><i>Trans</i>-effect</a> – Ligands in an octahedral or square planar complex are known to influence the reactivity of the group to which they are <i>trans</i>. This ligand influence is often referred to as the <i>trans</i>-influence, and it varies in intensity between ligands. A partial list of <i>trans</i>-influencing ligands is as follows, from highest <i>trans</i>-effect to lowest:<sup id="cite_ref-ACR_5-2" class="reference"><a href="#cite_note-ACR-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Aryl" class="mw-redirect" title="Aryl">aryl</a>, alkyl > NR<sub>3</sub> > PR<sub>3</sub> > AsR<sub>3</sub> > CO > <a href="/wiki/Chlorine" title="Chlorine">Cl</a>. Ligands with a greater <i>trans</i>-influence impart greater electrophilicity to the active site. Increasing the electrophilicity of the CO group has been shown experimentally to greatly increase the reaction rate, while decreasing the electrophilicity of the methyl group slightly increases the reaction rate. This can be demonstrated by reacting a square planar [(PN)M(CO)(CH<sub>3</sub>)] complex with CO, where PN is a <a href="/wiki/Bidentate" class="mw-redirect" title="Bidentate">bidentate</a> phosphorus- or nitrogen-bound ligand. This reaction proceeds in much greater yield when the methyl group is <i>trans</i>-P and the CO <i>trans</i>-N, owing to the higher <i>trans</i>-influence of the more electronegative nitrogen.<sup id="cite_ref-CCR_6-2" class="reference"><a href="#cite_note-CCR-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading3"><h3 id="Reverse_reaction">Reverse reaction</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Migratory_insertion&action=edit&section=4" title="Edit section: Reverse reaction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Decarbonylation" title="Decarbonylation">Decarbonylation</a> of <a href="/wiki/Aldehydes" class="mw-redirect" title="Aldehydes">aldehydes</a>, the reverse of CO insertion, is a well-recognized reaction: </p> <dl><dd>RCHO → RH + CO</dd></dl> <p>The reaction is not widely practiced in part because the <a href="/wiki/Alkanes" class="mw-redirect" title="Alkanes">alkanes</a> are less useful materials than are the aldehyde precursors. Furthermore, the reaction is not often conducted catalytically because the extruded CO can be slow to dissociate.<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> Extrusion of CO from an organic aldehyde is most famously demonstrated using <a href="/wiki/Wilkinson%27s_catalyst" title="Wilkinson's catalyst">Wilkinson's catalyst</a>:<sup id="cite_ref-OHNO_10-0" class="reference"><a href="#cite_note-OHNO-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>RhCl(PPh<sub>3</sub>)<sub>3</sub> + RCHO → RhCl(CO)(PPh<sub>3</sub>)<sub>2</sub> + RH + PPh<sub>3</sub></dd></dl> <p>Please see <a href="/wiki/Tsuji-Wilkinson_Decarbonylation_Reaction" class="mw-redirect" title="Tsuji-Wilkinson Decarbonylation Reaction">Tsuji-Wilkinson Decarbonylation Reaction</a> for an example of this elementary organometallic step in synthesis </p> <div class="mw-heading mw-heading3"><h3 id="Insertion_of_other_oxides">Insertion of other oxides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Migratory_insertion&action=edit&section=5" title="Edit section: Insertion of other oxides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many electrophilic oxides insert into metal carbon bonds; these include <a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">sulfur dioxide</a>, <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a>, and nitric oxide. These reactions have limited or no practical significance, but are of historic interest. With transition metal alkyls, these oxides behave as electrophiles and insert into the bond between metals and their relatively nucleophilic alkyl ligands. As discussed in the article on <a href="/wiki/Metal_sulfur_dioxide_complex" title="Metal sulfur dioxide complex">Metal sulfur dioxide complexes</a>, the insertion of SO<sub>2</sub> has been examined in particular detail. SO<sub>2</sub> inserts to give both <i>O</i>-sulphinates and <i>S</i>-sulphinates, depending on the metal centre.<sup id="cite_ref-DMA_11-0" class="reference"><a href="#cite_note-DMA-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> With square planar alkyl complexes, a pre-equilibrium is assumed involving formation of an adduct.<sup id="cite_ref-Puddephatt_12-0" class="reference"><a href="#cite_note-Puddephatt-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Insertion_of_alkenes_into_metal-carbon_bonds">Insertion of alkenes into metal-carbon bonds</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Migratory_insertion&action=edit&section=6" title="Edit section: Insertion of alkenes into metal-carbon bonds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The insertion of <a href="/wiki/Alkene" title="Alkene">alkenes</a> into both metal-carbon is important. The insertion of ethylene and propylene into titanium alkyls is the cornerstone of <a href="/wiki/Ziegler%E2%80%93Natta_catalysis" class="mw-redirect" title="Ziegler–Natta catalysis">Ziegler–Natta catalysis</a>, the main source of polyethylene and polypropylene. The majority of this technology involves heterogeneous catalysts, but it is widely assumed that the principles and observations on homogeneous systems are applicable to the solid-state versions. Related technologies include the <a href="/wiki/Shell_Higher_Olefin_Process" class="mw-redirect" title="Shell Higher Olefin Process">Shell Higher Olefin Process</a> which produces <a href="/wiki/Detergent" title="Detergent">detergent</a> precursors. </p> <dl><dd><figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:AlkeneInsMech%27.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/AlkeneInsMech%27.png/800px-AlkeneInsMech%27.png" decoding="async" width="800" height="144" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/AlkeneInsMech%27.png/1200px-AlkeneInsMech%27.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/41/AlkeneInsMech%27.png/1600px-AlkeneInsMech%27.png 2x" data-file-width="1941" data-file-height="349" /></a><figcaption>Steps in alkene polymerization. Step i involves binding of the monomer to the metal and step ii involves the migratory insertion step. These steps, which alternate from one side of the metal center to the other, are repeated many times for each polymer chain. The box represents a vacant (or extremely labile) coordination site.</figcaption></figure></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Mechanism">Mechanism</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Migratory_insertion&action=edit&section=7" title="Edit section: Mechanism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Factors affecting the rate of olefin insertions include the formation of the cyclic, planar, four-center <a href="/wiki/Transition_state" title="Transition state">transition state</a> involving incipient formation of a bond between the metal and an olefin carbon. From this transition state, it can be seen that a partial positive charge forms on the β-carbon with a partial negative charge formed on the carbon initially bonded to the metal. This polarization explains the subsequently observed formation of the bond between the negatively charged carbon/hydrogen and the positively charged β-carbon as well as the simultaneous formation of the metal-α-carbon bond. This transition state also highlights the two factors that most strongly contribute to the rate of olefin insertion reactions: (i) orbital overlap of the alkyl group initially attached to the metal and (ii) the strength of the metal-alkyl bond. With greater orbital overlap between the partially positive β-carbon and the partially negative hydrogen/alkyl group carbon, the formation of the new C-C bond is facilitated. With increasing strength of the metal-alkyl bond, the breaking of the bond between the metal and the hydrogen/alkyl carbon bond to form the two new bonds with the α-carbon and β-carbon (respectively) is slower, thus decreasing the rate of the insertion reaction.<sup id="cite_ref-Burger_et_al._13-0" class="reference"><a href="#cite_note-Burger_et_al.-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Insertion_of_alkenes_into_M–H_bonds"><span id="Insertion_of_alkenes_into_M.E2.80.93H_bonds"></span>Insertion of alkenes into M–H bonds</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Migratory_insertion&action=edit&section=8" title="Edit section: Insertion of alkenes into M–H bonds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The insertion of alkenes into metal-hydrogen bonds is a key step in <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a> and <a href="/wiki/Hydroformylation" title="Hydroformylation">hydroformylation</a> reactions. The reaction involves the alkene and the hydride ligands combining within the coordination sphere of a catalyst. In hydrogenation, the resulting alkyl ligand combines with a second hydride to give the alkane. Analogous reactions apply to the hydrogenation of alkynes: an alkenyl ligand combines with a hydride to eliminate an alkene. </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Beta-hydrideElim%26TS.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Beta-hydrideElim%26TS.png/600px-Beta-hydrideElim%26TS.png" decoding="async" width="600" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Beta-hydrideElim%26TS.png/900px-Beta-hydrideElim%26TS.png 1.5x, //upload.wikimedia.org/wikipedia/commons/7/7b/Beta-hydrideElim%26TS.png 2x" data-file-width="903" data-file-height="179" /></a><figcaption>Migratory insertion of an alkene into a metal hydride. The middle image depicts the transition state. Notice that the less substituted carbon becomes bonded to the metal, at least usually. The reverse reaction is called beta-hydride elimination.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Mechanism_2">Mechanism</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Migratory_insertion&action=edit&section=9" title="Edit section: Mechanism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In terms of mechanism, the insertion of alkenes into M–H bond and into M–C bonds are described similarly. Both involve four-membered transition states that place the less substituted carbon on the metal. </p><p>The reverse of olefin insertion into a metal-hydrogen bond is <a href="/wiki/Beta_elimination" class="mw-redirect" title="Beta elimination">β-hydride elimination</a>. The <a href="/wiki/Principle_of_Microscopic_Reversibility" class="mw-redirect" title="Principle of Microscopic Reversibility">Principle of Microscopic Reversibility</a> requires that the mechanism of β-hydride elimination follow the same pathway as the insertion of alkenes into metal hydride bonds. The first requirement for β-hydride elimination is the presence of a hydrogen at a position that is β with respect to the metal. β-elimination requires a vacant coordination position on the metal that will accommodate the hydrogen that is abstracted.<sup id="cite_ref-Crabtree_14-0" class="reference"><a href="#cite_note-Crabtree-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Industrial_applications">Industrial applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Migratory_insertion&action=edit&section=10" title="Edit section: Industrial applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Carbonylation">Carbonylation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Migratory_insertion&action=edit&section=11" title="Edit section: Carbonylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Two widely employed applications of migratory insertion of carbonyl groups are <a href="/wiki/Hydroformylation" title="Hydroformylation">hydroformylation</a> and the production of <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> by <a href="/wiki/Carbonylation" title="Carbonylation">carbonylation</a> of <a href="/wiki/Methanol" title="Methanol">methanol</a>. The former converts alkenes, hydrogen, and carbon monoxide into aldehydes. The production of acetic acid by carbonylation proceeds via two similar industrial processes. More traditional is the <a href="/wiki/Monsanto_process" title="Monsanto process">Monsanto acetic acid process</a>, which relies on a rhodium-iodine catalyst to transform methanol into acetic acid. This process has been superseded by the <a href="/wiki/Cativa_process" title="Cativa process">Cativa process</a> which uses a related iridium catalyst, [Ir(CO)<sub>2</sub>I<sub>2</sub>]<sup>−</sup> (<b>1</b>).<sup id="cite_ref-Cativa_15-0" class="reference"><a href="#cite_note-Cativa-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> By 2002, worldwide annual production of acetic acid stood at 6 million tons, of which approximately 60% is produced by the Cativa process.<sup id="cite_ref-Cativa_15-1" class="reference"><a href="#cite_note-Cativa-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Cativa-process-catalytic-cycle.png" class="mw-file-description" title="The catalytic cycle of the Cativa process"><img alt="The catalytic cycle of the Cativa process" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Cativa-process-catalytic-cycle.png/400px-Cativa-process-catalytic-cycle.png" decoding="async" width="400" height="351" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Cativa-process-catalytic-cycle.png/600px-Cativa-process-catalytic-cycle.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Cativa-process-catalytic-cycle.png/800px-Cativa-process-catalytic-cycle.png 2x" data-file-width="2150" data-file-height="1887" /></a><figcaption>The catalytic cycle of the Cativa process</figcaption></figure></dd></dl> <p>The Cativa process <a href="/wiki/Catalytic_cycle" title="Catalytic cycle">catalytic cycle</a>, shown above, includes both insertion and de-insertion steps. The oxidative addition reaction of <a href="/wiki/Methyl_iodide" class="mw-redirect" title="Methyl iodide">methyl iodide</a> with (<b>1</b>) involves the formal insertion of the iridium(I) centre into the carbon-iodine bond, whilst step (<b>3</b>) to (<b>4</b>) is an example of migratory insertion of carbon monoxide into the iridium-carbon bond. The active catalyst species is regenerated by the <a href="/wiki/Reductive_elimination" title="Reductive elimination">reductive elimination</a> of <a href="/wiki/Acetyl_iodide" title="Acetyl iodide">acetyl iodide</a> from (<b>4</b>), a de-insertion reaction.<sup id="cite_ref-Cativa_15-2" class="reference"><a href="#cite_note-Cativa-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Alkene_polymerization">Alkene polymerization</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Migratory_insertion&action=edit&section=12" title="Edit section: Alkene polymerization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Industrial applications of alkene insertions include metal-catalyzed routes to polyethylene and polypropylene. Typically these conversions are <a href="/wiki/Heterogeneous_catalysis" title="Heterogeneous catalysis">catalyzed heterogeneously</a> by titanium trichloride which are activated by aluminium alkyls. This technology is known as <a href="/wiki/Ziegler%E2%80%93Natta_catalyst" title="Ziegler–Natta catalyst">Ziegler–Natta catalysts</a>.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> In these reactions, ethylene coordinates to titanium metal followed by its insertion. These steps can be repeated multiple times, potentially leading to high molecular weight polymers. </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=Migratory_insertion&action=edit&section=13" 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 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="CITEREFElschenbroich2006" class="citation book cs1">Elschenbroich, C. (2006). <i>Organometallics</i>. Weinheim: Wiley-VCH. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-29390-2" title="Special:BookSources/978-3-527-29390-2"><bdi>978-3-527-29390-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organometallics&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2006&rft.isbn=978-3-527-29390-2&rft.aulast=Elschenbroich&rft.aufirst=C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMigratory+insertion" class="Z3988"></span></span> </li> <li id="cite_note-Hartwig-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-Hartwig_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHartwig2010" class="citation book cs1">Hartwig, J. F. (2010). <i>Organotransition Metal Chemistry, from Bonding to Catalysis</i>. 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