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 (free Supporting Information)
see article for more reactions
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.
see article for more examples
S. A. Babu, M. Yasuda, A. Baba, Org. Lett., 2007, 9, 405-408.