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Short Paper | Regular issue | Vol 87, No. 4, 2013, pp.827-840
Published online, 12th February, 2013
DOI: 10.3987/COM-13-12662
PREPARATION OF IMIDES vIA THE PALLADIUM-CATALYZED COUPLING REACTION OF ORGANOSTANNANES WITH METHYL N-[METHOXY(METHYLTHIO)METHYLENE]CARBAMATE

Kohei Orimoto, Takuhei Tomizawa, Yuki Namera, Harufumi Oyama, Takashi Niwa, and Masahisa Nakada*

*Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan

Abstract

The preparation of imides via the palladium-catalyzed coupling reaction of organostannanes is described. The palladium-catalyzed coupling reaction of aryl-, heteroaryl-, and alkenyl(tributyl)stannanes with methyl N-[methoxy(methylthio)methylene]carbamate in the presence of Cu(I) thiophene-2-carboxylate (CuTC) affords imino ethers, which are converted to the corresponding imides in high yield through acid hydrolysis.