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Communication | Regular issue | Vol 29, No. 6, 1989, pp.1013-1016
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4945
Palladium-catalyzed Indole and Benzofuran Ring Formation Accompanying Carbonylation

Yoshinori Kondo, Takao Sakamoto, and Hiroshi Yamanaka*

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

The reaction of 2-(1-hexynyl)aniline with carbon monoxide in methanol under basic conditions is promoted by the catalytic action of palladium dichloride to give methyl 2-butylindole-3-carboxylate. Similarly, the reaction of 2-(1-hexynyl)phenol under the same conditions gives methyl 2-butylbenzofuran-3-carboxylate. The carbonylative cyclization mentioned above is successful with the corresponding 2-phenylethynyl derivatives of aniline and phenol .