In(III)-Mediated Chemoselective Dehydrogenative Interaction of ClMe2SiH with Carboxylic Acids: Direct Chemo- and Regioselective Friedel-Crafts Acylation of Aromatic Ethers

Srinivasarao Arulananda Babu, Makoto Yasuda and Akio Baba*

*Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamada-oka, Suita, Osaka 565-0871, Japan, Email: babachem.eng.osaka-u.ac.jp

S. A. Babu, M. Yasuda, A. Baba, Org. Lett., 2007, 9, 405-408.

DOI: 10.1021/ol062723e (free Supporting Information)

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Abstract

A chemoselective reaction of ClMe₂SiH with carboxylic acids in the presence of InX₃ forms silyl esters (RCO₂Si(Cl)Me₂) as the major transient intermediates. A chemo- and regioselective Friedel-Crafts acylation of electron rich arenes with in situ formed silyl esters was established.

see article for more reactions

proposed mechanism

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Key Words

Friedel-Crafts Acylation

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ID: J54-Y2007-0320