New Insights into the Copper-Catalyzed Alkylation of Grignard and Organolithium Reagents

Gérard Cahiez*, Olivier Gager, Julien Buendia

*Department of Chemistry, CNRS Université de Paris 13, 74 Rue Marcel Cachin, 93017 Bobigny, France, Email: gerard.cahiezuniv-paris13.fr

G. Cahiez, O. Gager, J. Buendia, Synlett, 2010, 299-303.

DOI: 10.1055/s-0029-1219222

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Abstract

A slow and regular addition of primary alkyl and aryl Grignard reagent enables a high-yielding copper-catalyzed alkylation with alkyl bromides in the absence of ligands. With secondary and tertiary alkyl Grignard reagents, the presence of benzonitrile as a very simple ligand is sufficent. A copper-catalyzed alkylation of organolithium compounds was also studied.

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A New Efficient Catalytic System for the Chemoselective Cobalt-Catalyzed Cross-Coupling of Aryl Grignard Reagents with Primary and Secondary Alkyl Bromides

G. Cahiez, C. Chaboche, C. Duplais, A. Moyeux, Org. Lett., 2009, 11, 277-280.

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Key Words

alkylations (alkanes, arenes), copper, cross-coupling, Grignard reagents, organometallic reagents

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ID: J60-Y2010-0200