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The Corey–House Reaction: An Early Transition-Metal-Mediated Cross-Coupling
Selective Formation of Carbon–Carbon Bonds between Unlike Groups Using Organocopper Reagents.
J. Am. Chem. Soc. 1967;
18 March 2020 (online)
In 1967, Corey and Posner reported a simple method for carbon–carbon cross-coupling using the previously reported Gliman cuprates of type R2CuLi. In Corey’s original publication Me2CuLi was generated by adding MeLi to cuprous halides. The resulting dimethylcuprate was used for cross-couplings with alkyl, alkenyl, or aryl bromides and iodides to form the corresponding methylated products. trans-1-Bromo-2-phenylethylene was stereospecifically converted into trans-1-phenylpropene. In a similar fashion formation of cis-1-phenylpropene was observed from cis-1-bromo-2-phenylethylene.
In 1969 Whitesides, House, and co-workers contributed significantly to the scope of the coupling reaction by using lithium aryl-, sec-alkyl and tert-alkyl cuprates as coupling partners for the organic halides (G. M. Whitesides, W. F. Fischer Jr., J. San Filippo Jr., R. W. Bashe, H. O. House J. Am. Chem. Soc. 1969, 91, 4871). Thus, the cross-coupling reaction of Gilman cuprates with organyl halides is known as the Corey–House reaction. Variations of the name including Whitesides and Posner are also in use.