Zinc(II)-Catalyzed Addition of Grignard Reagents to Ketones

Manabu Hatano, Orie Ito, Shinji Suzuki and Kazuaki Ishihara*

*Graduate School of Engineering, Nagoya University, Email: ishiharacc.nagoya-u.ac.jp

M. Hatano, O. Ito, S. Suzuki, K. Ishihara, J. Org. Chem., 2010, 75, 5008-5016.

DOI: 10.1021/jo100563p

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Abstract

The use of ZnCl₂, Me₃SiCH₂MgCl, and LiCl effectively minimizes problematic side reactions in the 1,2-addition of strongly basic alkyl and aryl Grignard reagents to ketones. Aldimines give secondary amines in high yield. The simplicity of this reliable ZnCl₂•Me₃SiCH₂MgCl•LiCl system might be attractive for industrial as well as academic applications.

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Highly Efficient Alkylation to Ketones and Aldimines with Grignard Reagents Catalyzed by Zinc(II) Chloride

M. Hatano, S. Suzuki, K. Ishihara, J. Am. Chem. Soc., 2006, 128, 9998-9999.

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Key Words

1,2-addition to carbonyl compounds (arylation, alkylation), benzylamines, Grignard Reagents

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ID: J42-Y2010-2040