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Synthesis 2000; 2000(3): 429-434
DOI: 10.1055/s-2000-6354
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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
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Publication Date:
31 December 2000 (online)

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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

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