Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions

Xiu Wang, Zhenhua Wang, Li Liu, Yuya Asanuma, Yasushi Nishihara

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions was disclosed. A variety of aromatic acyl fluorides are capable of reacting with silylstannanes in the presence of cesium fluoride. A one-pot decarbonylative stannylation/Migita-Kosugi-Stille reaction of benzoyl fluoride, giving rise to the direct formation of the corresponding cross-coupled products, further demonstrated the synthetic utility of the present method. This newly developed methodology with a good functional-group compatibility via C-F bond cleavage and C-Sn bond formation under nickel catalysis opens a new area for the functionalization of acyl fluorides in terms of carbon-heteroatom bond formation.

Original languageEnglish
Article number1671
JournalMolecules
Volume24
Issue number9
DOIs
Publication statusPublished - Jan 1 2019

Keywords

  • Acyl fluorides
  • Carbon-tin bond formation
  • Decarbonylation
  • Nickel
  • Stannylation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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