The Barbier-Grignard-type carbonyl alkylation using unactivated alkyl halides in water

J Am Chem Soc. 2003 Apr 9;125(14):4062-3. doi: 10.1021/ja029649p.

Abstract

The aqueous Barbier-Grignard-type alkylation of aldehydes with unactivated alkyl iodides and bromides was developed. By using a combination of zinc and cuprous iodide, catalyzed by indium(I) chloride, we successfully added tertiary, secondary, and primary alkyl halides to various aromatic aldehydes in 0.07 M aqueous Na2C2O4. A mechanistic rationale for the success of the reaction has been proposed.