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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 (free Supporting Information)


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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.


Key Words

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


ID: J42-Y2010-2040