Synfacts 2020; 16(04): 0437
DOI: 10.1055/s-0040-1707676
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

The Corey–House Reaction: An Early Transition-Metal-Mediated Cross-Coupling

Paul Knochel
Johannes H. Harenberg
Corey EJ. * Posner GH. Harvard University, Cambridge, USA
Selective Formation of Carbon–Carbon Bonds between Unlike Groups Using Organocopper Reagents.

J. Am. Chem. Soc. 1967;
89: 3911-3912
Further Information

Publication History

Publication Date:
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.