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Article

Direct Coupling Reaction between Alcohols and Silyl Compounds: Enhancement of Lewis Acidity of Me₃SiBr Using InCl₃

Supporting Info

Takahiro Saito, Yoshihiro Nishimoto, Makoto Yasuda, and Akio Baba*

Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

J. Org. Chem., 2006, 71 (22), pp 8516–8522

DOI: 10.1021/jo061512k

Publication Date (Web): October 4, 2006

To whom correspondence should be addressed. Tel: +81-6-6879-7384. Fax: +81-6-6879-7387.

, baba@chem.eng.osaka-u.ac.jp

Abstract

The combination of InCl₃ and Me₃SiBr provided an enhanced Lewis acid system that can be used to promote a wide range of direct coupling reactions between alcohols and silyl nucleophiles in non-halogenated solvents, such as hexane or MeCN. The enhanced Lewis acidity of this system was measured by the ¹³C NMR in terms of the coordination to an alcohol. Moreover, the interaction between Me₃SiBr and the In(III) species was revealed by ²⁹Si NMR spectral analysis. Highly chemoselective allylations toward a hydroxyl moiety over ketone and acetoxy ones have been demonstrated.

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Published In Issue October 27, 2006
Received July 20, 2006

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Article

Direct Coupling Reaction between Alcohols and Silyl Compounds: Enhancement of Lewis Acidity of Me₃SiBr Using InCl₃