A direct synthesis of allenes by a traceless petasis reaction

Devon A. Mundal, Kelly E. Lutz, Regan J. Thomson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

58 Scopus citations

Abstract

A one-pot synthesis of allenes by the 2-nitrobenzenesulfonylhydrazide- mediated coupling of hydroxyaldehydes or ketones with alkynyl trifluoroborate salts is reported. This mild process involves in situ formation of a sulfonylhydrazone that reacts with alkynyl trifluoroborates to generate a transient propargylic hydrazide species. Decomposition of this unstable hydrazide via an intermediate monoalkyldiazine produces the allene products through an alkene walk mechanism.

Original languageEnglish (US)
Pages (from-to)5782-5785
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number13
DOIs
StatePublished - Apr 4 2012

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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