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

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, E-mail: babachem.eng.osaka-u.ac.jp

T. Saito, Y. Nishimoto, M. Yasuda, A. Baba, J. Org. Chem., 2006, 71, 8516-8522.

DOI: 10.1021/jo061512k (free Supporting Information)


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Abstract

An enhanced Lewis acid system of InCl3 and Me3SiBr can be used to promote a wide range of direct coupling reactions between alcohols and silyl nucleophiles in non-halogenated solvents. Highly chemoselective allylations toward a hydroxyl moiety over ketone and acetoxy ones have been demonstrated.

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Direct Carbon-Carbon Bond Formation from Alcohols and Active Methylenes, Alkoxyketones, or Indoles Catalyzed by Indium Trichloride

M. Yasuda, T. Somyo, A. Baba, Angew. Chem. Int. Ed., 2006, 45, 793-796.


Key Words

allylic substitutions, benzylic substitutions, 1,4-dienes, Hosomi-Sakurai reaction, alcohols, CC coupling, indium, synthetic methods


ID: J42-Y2006-3440