Alkyne carbonylation by radicals: Tin-radical-catalyzed synthesis of α-methylene amides from 1-alkynes, carbon monoxide, and amines

Yoshitaka Uenoyama*, Takahide Fukuyama, Osamu Nobuta, Hiroshi Matsubara, Ilhyong Ryu

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

118 Scopus citations

Abstract

A convergent synthesis of α-methylene amides exploits a hybrid radical/ionic concept in which radical carbonylation of alkynes is followed by ionic trapping of the resulting carbonyl-containing radical species with amines (see scheme). The reaction of substituted terminal alkynes with pressurized CO, Bu3SnH, and 2,2′-azobis-isobutyronitrile in the presence of a large excess of amines gave good yields of the corresponding α-methylene amides.

Original languageEnglish
Pages (from-to)1075-1078
Number of pages4
JournalAngewandte Chemie - International Edition
Volume44
Issue number7
DOIs
StatePublished - 4 Feb 2005

Keywords

  • Alkynes
  • Amides
  • Carbonylation
  • Radical Reactions
  • Tin

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