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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

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)


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



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

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


Key Words

Friedel-Crafts Acylation


ID: J54-Y2007-0320