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Note | Special issue | Vol 56, No. 1-2, 2002, pp.525-529
Published online, 1st January, 1970
DOI: 10.3987/COM-01-S(K)31
A Study for Palladium-catalyzed Chemoselective Vinylation at C-3 Position of 4-Bromo-1-tosylindole

Yuusaku Yokoyama,* Kazuhiro Tsuruta, and Yasuoki Murakami*

*School of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan

Abstract

Palladium-catalyzed direct activation of carbon-hydrogen bond at C-3 position of 4-bromo-1-tosylindole (1) was investigated. The reaction of 1 with ethyl acrylate (4) in the presence of 0.1 eq. of Pd(OAc)2 and MnO2-Cu(OAc)2-O2 system afforded C-3 vinylated product (5) in 52% yield, and by-products (6 and 7) that were formed by the Michael addition of AcOH or H2O to 5, were obtained in 17% and 7% yields respectively.