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Photoredox-Catalyzed Cross-Coupling of Enamides for the Assembly of β-Difluoroimine Synthons.

Jicheng WuMing LangJian Wang
Published in: Organic letters (2017)
A photoredox-catalyzed formal Csp3-Csp3 cross-coupling reaction of enamides with bromodifluoro compounds is established. The resulting gem-difluoromethylenated γ-imines indicated high stability, excellent E/Z control, and broad functional group tolerance. These synthetic intermediates can efficiently transfer to difluoromethylenated γ-amino acids or δ-amino alcohols. Mechanistic analysis indicates that a radical/SET mechanism proceeding via a difluoroalkyl radical may be involved in the catalytic cycle.
Keyphrases
  • room temperature
  • amino acid
  • visible light
  • electron transfer