☆ 4.4 Article

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

SYNLETT (2010)

Journal

SYNLETT

Volume -, Issue 2, Pages 299-303

Publisher

GEORG THIEME VERLAG KG

DOI: 10.1055/s-0029-1219222

Keywords

alkylations; copper; cross-coupling; Grignard reactions; organometallic reagents

Categories

Chemistry, Organic

Funding

Fondation de France (ESCOM)
Ministere de l'Education Nationale et de la Recherche
CNRS

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Abstract

Until now, it was considered that the copper-catalyzed alkylation of Grignard reagents gave good yields only in the presence of ligands, such as NMP or 1-phenylpropyne. We show herein that a slow and regular addition of the Grignard reagent provides similar results. With secondary and tertiary alkyl Grignard reagents, we disclosed that the presence of benzonitrile (10 mol%), a very simple ligand, is very efficient. The copper-catalyzed alkylation of organolithium compounds was also studied.

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