1,2-Migration of the thio group in allenyl sulfides: Efficient synthesis of 3-thio-substituted furans and pyrroles

Joseph T. Kim, Alexander V. Kel'In, Vladimir Gevorgyan

Research output: Contribution to journalArticlepeer-review

121 Scopus citations

Abstract

The copper-catalyzed cycloisomerization of thioalkynyl ketones 1 a and thioalkynyl imines 1b allows the efficient synthesis of 3-thio-substituted furans 3a and pyrroles 3b, an important class of heterocyclic unit previously inaccessible by standard cycloisomerization techniques. A plausible mechanism for this unusual cascade involves a 1,2-migration of the thio group in the intermediate keto- and iminoallenyl sulfides 2. DMA=N,N-dimethylacetamide.

Original languageEnglish (US)
Pages (from-to)98-101
Number of pages4
JournalAngewandte Chemie - International Edition
Volume42
Issue number1
DOIs
StatePublished - Jan 3 2003

Keywords

  • Cyclization
  • Heterocycles
  • Homogeneous catalysis
  • Nitrogen heterocycles
  • Sulfur

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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