Esters as Acylating Reagent in a Friedel-Crafts Reaction: Indium Tribromide Catalyzed Acylation of Arenes Using Dimethylchlorosilane

Yoshihiro Nishimoto, Srinivasarao Arulananda Babu, Makoto Yasuda and Akio Baba*

*Department of Applied Chemistry and Center for Atomic and Molecular Technologies (CAMT), Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan, Email: babachem.eng.osaka-u.ac.jp

Y. Nishimoto, S. A. Babu, M. Yasuda, A. Baba, J. Org. Chem., 2008, 73, 9465-9468.

DOI: 10.1021/jo801914x

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Abstract

A Friedel-Crafts acylation of arenes with esters has been achieved in the presence of dimethylchlorosilane and 10 mol % of indium tribromide . The key intermediate RCOOSi(Cl)Me₂ is generated from alkoxy esters with the evolution of the corresponding alkanes. The scope of the alkoxy ester moiety was wide: tert-butyl, benzyl, allyl, and isopropyl esters were successful.

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

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

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Key Words

Friedel-Crafts Acylation, Silanes

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ID: J42-Y2008-3710