One-pot synthesis of 2,5-dihydropyrroles from terminal alkynes, azides, and propargylic alcohols by relay actions of copper, rhodium, and gold

Tomoya Miura, Takamasa Tanaka, Kohei Matsumoto, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

46 Citations (Scopus)

Abstract

Relay actions of copper, rhodium, and gold formulate a one-pot multistep pathway, which directly gives 2,5-dihydropyrroles starting from terminal alkynes, sulfonyl azides, and propargylic alcohols. Initially, copper-catalyzed 1,3-dipolar cycloaddition of terminal alkynes with sulfonyl azides affords 1-sulfonyl-1,2,3-triazoles, which then react with propargylic alcohols under the catalysis of rhodium. The resulting alkenyl propargyl ethers subsequently undergo the thermal Claisen rearrangement to give a-allenyl-a-amino ketones. Finally, a gold catalyst prompts 5-endo cyclization to produce 2,5-dihydropyrroles.

Original languageEnglish
Pages (from-to)16078-16082
Number of pages5
JournalChemistry - A European Journal
Volume20
Issue number49
DOIs
Publication statusPublished - Jan 12 2014
Externally publishedYes

Keywords

  • Copper
  • Gold
  • Rhodium
  • Terminal alkynes
  • Triazoles

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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