Gold(i)-catalyzed 6-endo-dig azide-yne cyclization: efficient access to 2H-1,3-oxazines

Geoffroy Hervé Lonca, Ciputra Tejo, Hui Ling Chan, Shunsuke Chiba*, Fabien Gagosz

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

54 Citations (Scopus)

Abstract

Denitrogenative 6-endo-dig azide-yne cyclization of α-propargyloxy-β-haloalkylazides was enabled by gold catalysis, thus providing 2H-1,3-oxazines. This rare cyclization mode in gold-catalyzed reactions of azide-yne substrates was demonstrated to be facilitated and controlled by electronic and resonance effects of the alkyne substituents. Molecular transformations of the as-prepared 2H-1,3-oxazines were also investigated.

Original languageEnglish
Pages (from-to)736-739
Number of pages4
JournalChemical Communications
Volume53
Issue number4
DOIs
Publication statusPublished - 2017
Externally publishedYes

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry.

ASJC Scopus Subject Areas

  • Electronic, Optical and Magnetic Materials
  • Catalysis
  • Ceramics and Composites
  • General Chemistry
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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