Gold-catalyzed intramolecular carbothiolation of alkynes: Synthesis of 2,3-disubstituted benzothiophenes from (α-alkoxy alkyl) (ortho-alkynyl phenyl) sulfides

Itaru Nakamura, Takuma Sato, Yoshinori Yamamoto

Research output: Contribution to journalArticlepeer-review

272 Citations (Scopus)

Abstract

(Chemical Equation Presented) Gold forms rings: AuCl-catalyzed cyclization of (α-alkoxy alkyl) (ortho-alkynyl phenyl) Sulfides 1 proceeds under mild conditions to give 3-(α-alkoxy alkyl) benzothiophenes 2 in high yields for a wide range of substrates (see scheme). The starting materials are readily available through acetalization of ortho-bromobenzenethiol and subsequent Sonogashira coupling. This methodology provides an atom-economic route to sulfur-containing heteroarenes.

Original languageEnglish
Pages (from-to)4473-4475
Number of pages3
JournalAngewandte Chemie - International Edition
Volume45
Issue number27
DOIs
Publication statusPublished - 2006 Jul 3

Keywords

  • Cyclization
  • Gold
  • Homogeneous catalysis
  • Sulfur heterocycles
  • Synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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