New Preparation of Benzylic Aluminum and Zinc Organometallics by Direct Insertion of Aluminum Powder

Tobias D. Blümke, Klaus Groll, Konstantin Karaghiosoff and Paul Knochel*

*Department Chemie, Ludwig-Maximilians-Universität, Butenandtstrasse, 5-13, 81377 München, Germany, Email: Paul.Knochelcup.uni-muenchen.de

T. D. Blümke, K. Gross, K. Karaghiosoff, P. Knochel, Org. Lett., 2011, 13, 6440-6443.

DOI: 10.1021/ol202733v

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Abstract

The reaction of benzylic chlorides with Al-powder in the presence of InCl₃ as catalyst provides various functionalized benzylic aluminum sesquichlorides under mild conditions. These organometallics reacted smoothly in Pd-catalyzed cross-couplings, or Cu-mediated acylations, allylations, or 1,4-addition reactions. Substrates prone to Wurtz coupling can be converted to benzylic zinc compounds first.

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Key Words

Diarylmethanes

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ID: J54-Y2011-3620