Download PDF
Synthesis 2000; 2000(3): 429-434
DOI: 10.1055/s-2000-6354
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Synthesis of 2,3-Disubstituted Indoles by Palladium-Mediated Coupling of 2-Iodoindoles

Hidetoshi Tokuyama* , Yosuke Kaburagi, Xiaoqi Chen, Tohru Fukuyama
  • *Graduate School of Pharmaceutical Sciences, The University of Tokyo CREST, The Japan Science and Technology Corporation, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan; Fax + 81(3)58 02 86 94; E-mail: fukuyama@mol.f.u-tokyo-ac.jp
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

N-Unprotected 2-iodoindoles are synthesized by treatment of 2-stannylindoles with iodine, which in turn are prepared by tin-mediated radical cyclization of 2-alkenylphenylisocyanides. Palladium-catalyzed coupling reactions of N-unprotected 2-iodoindoles with terminal acetylenes, terminal olefins, carbonylation, and the Suzuki coupling reaction with phenyl borate proceed smoothly to furnish the corresponding 2,3-disubstituted indoles in good to excellent yields.

2-iodoindole - 2-stannylindole - isonitrile - radical cyclization - palladium-mediated coupling