{"id":9484,"date":"2016-01-29T15:07:18","date_gmt":"2016-01-29T20:07:18","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=9484"},"modified":"2026-05-07T06:18:39","modified_gmt":"2026-05-07T11:18:39","slug":"gilman-reagents-organocuprates-how-theyre-made","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2016\/01\/29\/gilman-reagents-organocuprates-how-theyre-made\/","title":{"rendered":"Organocuprates (Gilman Reagents): How They&#8217;re Made"},"content":{"rendered":"<p><strong>How Gilman Reagents (Organocuprates) Are Made<\/strong><\/p>\n<ul>\n<li>Gilman reagents (organocuprates, often written as &#8220;R<sub>2<\/sub>CuLi&#8221; are\u00a0<strong>not<\/strong> made the same way as Grignard or organolithium reagents.<\/li>\n<li>Instead of being made from alkyl halides, they are made through the reaction of an alkyllithium with a copper salt (e.g. CuBr)<\/li>\n<li>The use of\u00a0<strong>two\u00a0<\/strong>equivalents of alkyllithium (R-Li) relative to copper (CuX) is important for forming the organocuprate<\/li>\n<li>If only one equivalent is used, the result is an &#8220;organocopper&#8221; reagent (R-Cu) which is a poor nucleophile.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-34486\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/04\/0-summary-of-how-gilman-reagents-are-made-from-copper-1-salts-and-two-equivalents-of-organolithium-reagents.gif\" alt=\"summary of how gilman reagents are made from copper 1 salts and two equivalents of organolithium reagents\" width=\"640\" height=\"647\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Organometallics: What About The Rest Of The Periodic Table?<\/a><\/li>\n<li><a href=\"#two\">Can We Make Other Organometallics The Same Way We Make Grignards (And Organolithiums)?<\/a><\/li>\n<li><a href=\"#three\">Formation of Organometallics From Alkyl Halides Involves Reduction<\/a><\/li>\n<li><a href=\"#four\">Direct Formation of Organometallics From Cu Is Much More Difficult Than From Mg or Li<\/a><\/li>\n<li><a href=\"#five\">A Work-Around: Transmetallation<\/a><\/li>\n<li><a href=\"#six\">OrganoCOPPER reagents: Way Less Reactive Than Grignards<\/a><\/li>\n<li><a href=\"#seven\">OrganoCUPRATES: The Much-More-Reactive Cousins of OrganoCOPPER Reagents<\/a><\/li>\n<li><a href=\"#eight\">Summary: Organocuprates<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quizzes\">Quiz Yourself!<\/a><\/li>\n<li><a href=\"#references\">(Advanced) References and Further Reading<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><a id=\"one\"><\/a>1. Organometallics: What About The Rest Of The Periodic Table?<\/h2>\n<p>In this whole series on organometallics so far has covered exactly TWO metals: lithium and magnesium (with a very brief head-nod to sodium and the comparatively useless\u00a0<del>Wurzt<\/del> <a href=\"https:\/\/en.wikipedia.org\/wiki\/Wurtz_reaction\">Wurtz reaction<\/a>.)<\/p>\n<p>There are dozens of other metals on the periodic table. What about organometallic compounds of <strong><em>them<\/em><\/strong> ?<\/p>\n<p>Great question! (<span style=\"color: #993366;\"><em>That&#8217;s also the first thing you say when someone asks you a question you want to dodge.<\/em><\/span>)<\/p>\n<p><strong>Much as we&#8217;d love to<\/strong>, we just don&#8217;t have enough time to get into the full glory of organometallic chemistry in an introductory course. \u00a0(<span style=\"color: #993366;\"><em>If you&#8217;re curious, may I suggest <a style=\"color: #993366;\" href=\"https:\/\/organometallicchem.wordpress.com\">The Organometallic Reader<\/a><strong>?<\/strong><\/em><\/span>)<\/p>\n<p>In this post and the next we&#8217;ll give perfunctory treatment of some organometallic compounds of copper, and perhaps in a later post have something cranky to say about palladium, and call it a series.<\/p>\n<p>Let&#8217;s get started.<\/p>\n<h2><a id=\"two\"><\/a>2. Can We Make Other Organometallics The Same Way We Make Grignards And Organolithiums?<\/h2>\n<p>First, recall what we&#8217;ve said so far about how to make organometallic compounds: basically, take an organohalide, add magnesium or lithium, and stir. (<em>See post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/11\/09\/synthesis-of-grignard-and-organolithium-reagents\/\">Synthesis of organolithium and Grignard reagents<\/a><\/em>)<\/p>\n<p>You might wonder: is it this easy for making other organometallics?<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15375\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-grignard-reagents-and-organolithium-reagents-are-made-through-reduction-with-li-metal-or-mg-metal-in-solvents-does-not-work-well-for-cu.gif\" alt=\"grignard reagents and organolithium reagents are made through reduction with li metal or mg metal in solvents does not work well for cu\" width=\"600\" height=\"383\" \/><\/p>\n<p>The short answer is: <strong>for most metals, it doesn&#8217;t work nearly as well.<\/strong><\/p>\n<h2><a id=\"three\"><\/a>3. Formation of Organometallics From Alkyl Halides Involves Reduction<\/h2>\n<p>Remember that formation of organometallic compounds from organohalides is a\u00a0<em>reduction\u00a0<\/em>reaction. Here it&#8217;s illustrated for the synthesis of organolithium compounds.<br \/>\n<img decoding=\"async\" class=\"alignnone wp-image-15376\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-formation-of-organolithium-from-alkyl-halide-is-a-reduction-reaction.gif\" alt=\"formation of organolithium from alkyl halide is a reduction reaction\" width=\"600\" height=\"142\" \/><\/p>\n<p>Notice how the polarity on the carbon changed from positive to negative? Not that we normally do such things, but if you keep track of the carbon oxidation state, you&#8217;d see that it changed from (\u20132) to (\u20134). (<em>See post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/07\/25\/calculating-the-oxidation-state-of-a-carbon\/\">Calculating the oxidation state of carbon<\/a><\/em>)<\/p>\n<p>This works well for lithium and magnesium because <strong>those metals are so easily oxidized<\/strong>. We can quantify this by looking at a table of oxidation potentials.<\/p>\n<p>See how lithium, sodium, and magnesium are near the top of this table of oxidation potentials for metals? They&#8217;re <strong>easily oxidized<\/strong> &#8211; which means they are extremely <strong>strong reductants<\/strong>.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15377\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-compared-to-most-metals-lithium-and-magnesium-are-very-strong-reducing-agents-and-copper-is-a-poor-reducing-agent.gif\" alt=\"compared to most metals lithium and magnesium are very strong reducing agents and copper is a poor reducing agent\" width=\"630\" height=\"528\" \/><\/p>\n<p><span style=\"color: #993366;\"><em>[note that these voltages are in aqueous solution, so take these numbers with a grain of salt for reactions performed in organic solvents].<\/em><\/span><\/p>\n<p>As we move from lithium down the table to metals like nickel and copper, we should expect the reduction reaction should become progressively more difficult. And it is!<\/p>\n<h2><a id=\"four\"><\/a>4. Direct Formation Of Organometallics From Metals Like Cu Is Much More Difficult Than For Mg or Li<\/h2>\n<p>In other words,\u00a0direct formation of an organometallic from the organohalide and that metal <span style=\"color: #993366;\"><em>[a process we call &#8216;insertion&#8217; , or &#8220;oxidative addition&#8221;, FYI]<\/em><span style=\"color: #000000;\"> is less favoured.<\/span><\/span><\/p>\n<p>Look at copper for instance: the &#8220;direct reduction&#8221; doesn&#8217;t work nearly as well as it does for Li and Mg.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15378\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-direct-formation-of-organometallics-from-alkyl-halides-with-copper-does-not-work-very-well.gif\" alt=\"direct formation of organometallics from alkyl halides with copper does not work very well\" width=\"600\" height=\"255\" \/><\/p>\n<p>I don&#8217;t mean to imply that it\u00a0<em>can&#8217;t\u00a0<\/em>be done, but it generally requires heat and the addition of extra reagents that influence the oxidation potential of the metal (<span style=\"color: #993366;\"><em>these are called <a href=\"https:\/\/en.wikipedia.org\/wiki\/Ligand\">ligands<\/a><\/em><\/span>) \u00a0in order to get this reaction to go.<\/p>\n<h2><a id=\"five\"><\/a>5. A Work-Around: Transmetallation<\/h2>\n<p>Let&#8217;s say we really need to make an organometallic compound of copper. Can we get around this difficulty we generally experience in direct reduction? Yes &#8211; there&#8217;s a workaround.<\/p>\n<p>What we can do instead is to start with a <strong>pre-made<\/strong> organometallic (such as an organolithium or Grignard reagent) where the reduction has <strong>already occurred<\/strong>. We can then add a copper (I) salt such as CuBr or CuCl.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15379\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-a-workaround-to-reduction-by-copper-is-to-make-organocuprates-from-transmetallation-with-cu-and-organolithium-or-grignard.gif\" alt=\"a workaround to reduction by copper is to make organocuprates from transmetallation with cu and organolithium or grignard\" width=\"600\" height=\"335\" \/><\/p>\n<p>The result is displacement of the halide at copper by the carbon bound to lithium, and we form an organocopper reagent (plus a lithium salt). [<span style=\"color: #993366;\"><em>You might wonder: why does this work at all? <a style=\"color: #993366;\" href=\"#noteone\">Note 1<\/a>.<\/em> <\/span>]<\/p>\n<p>Yahoo for shortcuts!!<\/p>\n<p>(<span style=\"color: #993366;\"><em>Although not shown, this also works for Grignard reagents<\/em><\/span>)<\/p>\n<p>Now that we have a way to make organocopper reagents, the next question is: <strong>so what?<\/strong> What can we\u00a0<em>do\u00a0<\/em>with them?<\/p>\n<h2><strong><a id=\"six\"><\/a>6. Organocopper Reagents: WAY Less Reactive Than Grignards<\/strong><\/h2>\n<p>In comparison to Grignard and organolithium reagents which are <a href=\"https:\/\/www.youtube.com\/watch?v=kRm0Hm33lDE\">violently destroyed<\/a> by water (and sometimes air)\u00a0organocopper reagents are fairly sedate. For instance, there are organocopper reagents that you can leave out in the air without incident, like 1-hexynylcopper.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15380\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-organocopper-reagents-are-quite-inert-for-example-hexynylcopper-is-bench-stable-compare-to-tert-butyl-lithium.gif\" alt=\"organocopper reagents are quite inert for example hexynylcopper is bench stable compare to tert butyl lithium\" width=\"600\" height=\"130\" \/><\/p>\n<p>Also, organocopper reagents\u00a0don\u2019t add to\u00a0carbonyls or epoxides like\u00a0organolithium reagents or Grignard reagents do.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15381\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/7-what-can-ogranocopper-reagents-be-used-for-wont-react-with-aldehydes-or-epoxides.gif\" alt=\"what can ogranocopper reagents be used for - wont react with aldehydes or epoxides\" width=\"600\" height=\"334\" \/><\/p>\n<p>While organo<strong>copper<\/strong> reagents are interesting, it turns out that they have a chemical &#8220;cousin&#8221; that is even more versatile, reactive, and useful, and for that reason we will from this point further focus on these species: &#8220;organo<strong>cuprate<\/strong>&#8221; reagents.<\/p>\n<h2><a id=\"seven\"><\/a>7. Organocuprates: Far More Reactive &#8220;Cousins&#8221; Of Organocopper Reagents<\/h2>\n<p>In the 1940&#8217;s Iowa chemist Henry Gilman discovered that adding one further equivalent of an organolithium reagent to an organocopper compound resulted in an &#8220;organo<strong>cuprate<\/strong>&#8221; reagent, with two Cu\u2013C bonds and is also comprised of a positive counter-ion (lithium in this case).<\/p>\n<p>[<span style=\"color: #993366;\"><em>Note that &#8220;-ate&#8221; at the end. Notice how many species that end in the name &#8220;ate&#8221; \u00a0[e.g. sulfate, nitrate, tosylate] are negatively charged?<\/em><\/span>]<\/p>\n<p>Organo<strong>cuprates<\/strong>, with the general formula R<sub>2<\/sub>CuLi , have the same general pattern of reactivity as organocopper reagents, but are<strong> much more reactive. <\/strong>These compounds\u00a0are commonly referred to as &#8220;Gilman reagents&#8221; in ol&#8217; H.G.&#8217;s honour. [<span style=\"color: #993366;\"><em>Why are they more reactive? <a href=\"#notetwo\">Note 2<\/a><\/em><\/span>].<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15382\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/8-gilman-contribution-was-adding-second-equivalent-of-organolithium-to-organocopper-reagent-made-organocopper-which-is-far-more-reactive-and-useful-than-organocopper-r2culi.gif\" alt=\"gilman contribution was adding second equivalent of organolithium to organocopper reagent made organocopper which is far more reactive and useful than organocopper r2culi\" width=\"600\" height=\"339\" \/><\/p>\n<p>Just like organocopper reagents (and in contrast to Grignards) <strong>organocuprates do not generally add to aldehydes, ketones, or esters.\u00a0<\/strong><\/p>\n<p>However, as we&#8217;ll see in the next post, \u00a0they\u00a0<strong>do<\/strong> participate in substitution and &#8220;conjugate addition&#8221; reactions &#8211; <strong>reactions that Grignards and organolithiums reagents typically don&#8217;t do.<\/strong>\u00a0In this way (as we&#8217;ll see) they have a somewhat complimentary function.<\/p>\n<h2><a id=\"eight\"><\/a>8. Summary: Synthesis of Organocuprates<\/h2>\n<p>Let&#8217;s sum up. We saw that we generally don&#8217;t make organocopper reagents directly, but via organolithium or Grignard reagents. However, there&#8217;s an even more reactive &#8220;cousin&#8221; of organocopper reagents &#8211; &#8220;organocuprates&#8221; &#8211; that we can also make\u00a0if we use a 2:1 ratio of organolithium to copper.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15383\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/9-synthesis-of-gilman-reagents-form-alkyl-halides-via-addition-of-organolithium-reagents-to-copper-salts.gif\" alt=\"synthesis of gilman reagents form alkyl halides via addition of organolithium reagents to copper salts\" width=\"600\" height=\"434\" \/><\/p>\n<p>Note again: you need\u00a0<strong>two<\/strong> equivalents of organolithium for every equivalent of copper.<\/p>\n<p>Also note that you can use various different Cu(I) salts, as well as Grignard reagents.<\/p>\n<p>So what&#8217;s so great about Gilman reagents, and what can they be used for?<\/p>\n<p>We&#8217;ll talk about that in the next post. See you next time!<\/p>\n<p><strong><a href=\"https:\/\/www.masterorganicchemistry.com\/2016\/02\/05\/gilman-reagents-organocuprates-what-theyre-used-for\/\">Next Post: Reactions Of Gilman Reagents<\/a><\/strong><\/p>\n<hr \/>\n<h2><strong><a id=\"notes\"><\/a>Notes<\/strong><\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2016\/02\/05\/gilman-reagents-organocuprates-what-theyre-used-for\/\" class=\"\"><span>Gilman Reagents (Organocuprates): What They\u2019re Used For<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/11\/09\/synthesis-of-grignard-and-organolithium-reagents\/\" class=\"\"><span>Formation of Grignard and Organolithium Reagents<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/04\/12\/what-makes-a-good-leaving-group\/\" class=\"\"><span>What makes a good leaving group?<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/07\/25\/calculating-the-oxidation-state-of-a-carbon\/\" class=\"\"><span>Calculating the oxidation state of a carbon<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2016\/01\/19\/grignard-reactions-and-synthesis-2\/\" class=\"\"><span>Grignard Reactions And Synthesis (2)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2016\/04\/11\/reaction-map-reactions-of-organometallics\/\" class=\"\"><span>Reaction Map: Reactions of Organometallics<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/12\/10\/reactions-of-grignard-reagents\/\" class=\"\"><span>1,4-addition of organocuprates (Gilman reagents) to enones (MOC Membership)<\/span><\/a><\/li><\/ul><\/div>\n<p><strong>Bonus question for today<\/strong>. What&#8217;s the oxidation state of Cu in Gilman reagents?<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15384\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F1-quiz-what-is-oxidation-state-of-copper-in-gilman-reagent-r2cuLi.gif\" alt=\"quiz what is oxidation state of copper in gilman reagent r2cuLi\" width=\"600\" height=\"228\" \/><\/p>\n<p><strong><a id=\"noteone\"><\/a>Note 1<\/strong>. Why does transmetallation from lithium (or magnesium) to copper work? It&#8217;s a good question.\u00a0In a nutshell, the carbon-copper bond is stronger than the C-Li or C-Mg bond, and that provides the driving force.<\/p>\n<p>Why is the C-Cu bond stronger than C-Li ? That&#8217;s a\u00a0difficult question to answer succinctly, but I&#8217;ll try.<\/p>\n<p>You can think of bonding as having two components:<\/p>\n<ol>\n<li>\u00a0an electrostatic component, where there is attraction between opposite charges (such as in salts)<\/li>\n<li>the overlap of molecular orbitals, resulting in shared electron density between atoms.<\/li>\n<\/ol>\n<p>Bonding between a carbanion \u00a0R<sup>\u2013 \u00a0<\/sup>with Li+ is almost purely ionic (note the electronegativity difference of about 1.5) meaning that a significant portion of the bonding interaction is due to electrostatic interactions.<\/p>\n<p>In contrast, \u00a0bonding between C and Cu is considerably more covalent. There&#8217;s less of an electronegativity difference (Cu 1.9 vs. C 2.5) and the bonding is better described by metal-carbon bond overlap.<\/p>\n<p>[waves hands] Generally, carbon forms stronger bonds through orbital overlap than via electrostatic interactions. This is largely because carbon is significantly more polarizable (the negative charge is &#8220;squishy&#8221;, or &#8220;diffuse&#8221; &#8211; we often use the shorthand &#8220;soft&#8221; to describe this behaviour) than a generally non-polarizable (&#8220;hard&#8221;) atom like lithium or oxygen. Likewise copper is also a fairly &#8220;soft&#8221; atom.<\/p>\n<p>If you want to get super technical, for C-Cu the covalent term in the <a href=\"http:\/\/www.chemie.uni-mainz.de\/Praktikum\/AC\/AC1\/pdf\/klopman_salem.pdf\">Klopman equation<\/a> is large, and the coulombic term is small.<\/p>\n<p><strong><a id=\"notetwo\"><\/a>Note 2.\u00a0<\/strong>Organocuprate reaagents are more reactive than organocopper reagents because after transferring R(-), the result will be a neutral organocopper reagent. After organocopper reagents transfer R(-) the result will be an electron-deficient copper ion.<\/p>\n<hr \/>\n<h2><a id=\"quizzes\"><\/a>Quiz Yourself!<\/h2>\n<p><br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3085-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p>&nbsp;<\/p>\n<p>&nbsp;<\/p>\n<hr \/>\n<p><strong><a id=\"references\"><\/a>(Advanced) References and Further Reading<\/strong><\/p>\n<ol>\n<li><strong>The Preparation of Methylcopper and some Observations on the Decomposition of Organocopper Compounds<br \/>\n<\/strong>Henry Gilman, Reuben G. Jones, and L. A. Woods.<br \/>\n<em>The Journal of Organic Chemistry\u00a0<\/em><strong>1952\u00a0<\/strong><em>17\u00a0<\/em>(12), 1630-1634<br \/>\n<strong>DOI:\u00a0<\/strong><a href=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jo50012a009\">10.1021\/jo50012a009<\/a><br \/>\nOne of the first papers by Prof. Henry Gilman (U. of Iowa) on \u2018Gilman Reagents\u2019 \u2013 diorganocopper compounds. In this case he describes the preparation of dimethylcopper.Over the decades, a <em>lot<\/em>of people have carried out a lot of work in order to elucidate the true nature of copper intermediates and various copper species in reactions. There is a lot of literature in this area, and this is barely scratching the surface:<\/li>\n<li><strong>The composition of lithium methylcuprates in ether solvents<br \/>\n<\/strong> C. Ashby and John J. Watkins.<br \/>\n<em>Journal of the American Chemical Society\u00a0<\/em><strong>1977\u00a0<\/strong><em>99\u00a0<\/em>(16), 5312-5317<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ja00458a015\">10.1021\/ja00458a015<\/a><\/li>\n<li><strong>Mechanism of thermal decomposition of n-butyl(tri-n-butylphosphine) copper(I)<br \/>\n<\/strong>George M. Whitesides, Erwin R. Stedronsky, Charles P. Casey, and Joseph San Filippo Jr.<br \/>\n<em>Journal of the American Chemical Society\u00a0<\/em><strong>1970\u00a0<\/strong><em>92\u00a0<\/em>(5), 1426-1427<strong><br \/>\nDOI:\u00a0<\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ja00708a067\">10.1021\/ja00708a067<\/a><\/li>\n<li><strong>The Chemistry of Carbanions. XII. The Role of Copper in the Conjugate Addition of Organometallic Reagents<sup>1<\/sup><br \/>\n<\/strong>Herbert O. House, William L. Respess, and George M. Whitesides<b>.<br \/>\n<\/b><em>The Journal of Organic Chemistry\u00a0<\/em><strong>1966\u00a0<\/strong><em>31\u00a0<\/em>(10), 3128-3141<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo01348a012\">10.1021\/jo01348a012<\/a><\/li>\n<li><strong>Autocatalytic decomposition of alkylcopper(I) species. Electron spin resonance spectrum of binuclear copper(O) intermediates<br \/>\n<\/strong>Jay K. Kochi, Keisuke Wada, and Masuhiko Tamura.<br \/>\n<em>Journal of the American Chemical Society\u00a0<\/em><strong>1970\u00a0<\/strong><em>92\u00a0<\/em>(22), 6656-6658<strong><br \/>\nDOI:\u00a0<\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ja00725a055\">10.1021\/ja00725a055<\/a><\/li>\n<li><strong>Chemistry of carbanions. XVII. Addition of methyl organometallic reagents to cyclohexenone derivatives<br \/>\n<\/strong>Herbert O. House and William F. Fischer Jr.<br \/>\n<em>The Journal of Organic Chemistry\u00a0<\/em><strong>1968\u00a0<\/strong><em>33\u00a0<\/em>(3), 949-956<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jo01267a004\">10.1021\/jo01267a004<\/a><\/li>\n<\/ol>\n<hr \/>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>How Gilman Reagents (Organocuprates) Are Made Gilman reagents (organocuprates, often written as &#8220;R2CuLi&#8221; are\u00a0not made the same way as Grignard or organolithium reagents. Instead of <\/p>\n","protected":false},"author":1,"featured_media":15374,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1102],"tags":[299,1091,1089,1090,347,266],"post_folder":[],"class_list":["post-9484","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-organometallics","tag-alkyl-halides","tag-gilman-reagents","tag-organocopper","tag-organocuprates","tag-organometallics","tag-reduction"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Organocuprates (Gilman Reagents): How They&#039;re Made<\/title>\n<meta name=\"description\" content=\"Organocuprates (&quot;Gilman Reagents&quot;) have the general structure R2CuLi, where R is a carbon group. They&#039;re made from alkyllithium species. 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