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Added-Metal-Free Catalytic Nucleophilic Addition of Grignard Reagents to Ketones

Hua Zong, Huayin Huang, Junfeng Liu, Guangling Bian and Ling Song*

*The State Key Lab of Structural Chemistry, The Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China, Email: songlingfjirsm.ac.cn

H. Zong, H. Huang, J. Liu, G. Bian, L. Song, J. Org. Chem., 2012, 77, 4645-4652.

DOI: 10.1021/jo3004277 (free Supporting Information)


Abstract

A combinational effect of quaternary ammonium salts and organic bases enables an added-metal-free catalytic system for nucleophilic addition reactions of a variety of Grignard reagents to diverse ketones in THF as solvent to produce tertiary alcohols in good yields. By using tetrabutylammonium chloride as a catalyst and diglyme as an additive, this system strongly enhances the efficiency of addition at the expense of enolization and reduction.

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Key Words

Grignard Reaction, 1,2-addition


ID: J42-Y2012-1470