Autotandem catalysis: Synthesis of pyrroles by gold-catalyzed cascade reaction

Hirofumi Ueda, Minami Yamaguchi, Hiroshi Kameya, Kenji Sugimoto, Hidetoshi Tokuyama

Research output: Contribution to journalArticlepeer-review

57 Citations (Scopus)

Abstract

A novel synthesis of substituted pyrroles by a gold(I)-catalyzed cascade reaction has been developed. The reaction proceeded with an autotandem catalysis consisting of an initial addition of gold-acetylide to an acetal moiety and was followed by gold-catalyzed 5-endo-dig cyclization and aromatization. Gold catalysts play a dual role in activating nucleophilicity or electrophilicity of terminal acetylenes by forming gold-acetylides or by π-coordination. The formal (3 + 2) annulation of two components provided a variety of substituted pyrroles in a modular fashion.

Original languageEnglish
Pages (from-to)4948-4951
Number of pages4
JournalOrganic letters
Volume16
Issue number18
DOIs
Publication statusPublished - 2014 Sep 19

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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