Synthesis of 2,3-disubstituted indoles by palladium-mediated coupling of 2-iodoindoles

Hidetoshi Tokuyama, Yosuke Kaburagi, Xiaoqi Chen, Tohru Fukuyama

Research output: Contribution to journalArticlepeer-review

67 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)429-434
Number of pages6
JournalSynthesis
Issue number3
DOIs
Publication statusPublished - 2000
Externally publishedYes

Keywords

  • 2-iodoindole
  • 2-stannylindole
  • Isonitrile
  • Palladium- mediated coupling
  • Radical cyclization

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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