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March 26, 2026Organic Letters3 citations

Phosphine-Catalyzed Visible-Light-Induced Aminodifluoroalkylation of Alkenes: Access to α,α-Difluoro-γ-lactams

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LWLimin WangXLXiang LianCLChangjie Liu

Key Points

  • The research aims to establish a method for synthesizing α,α-difluoro-γ-lactams using visible light and phosphine catalysis.
  • Developed a visible-light-induced radical cyclization technique.
  • Utilized α-bromodifluoroacetamides and olefins as starting materials.
  • Conducted mechanistic studies to explore the reaction pathway.
  • Achieved moderate to good yields of α,α-difluoro-γ-lactams.
  • Demonstrated excellent functional-group compatibility.
  • Supported a nonchain radical pathway involving an electron donor-acceptor complex.

Abstract

A visible-light-induced, phosphine-catalyzed radical cyclization of α-bromodifluoroacetamides with various olefins has been established for the efficient synthesis of α,α-difluoro-γ-lactams. This protocol offers mild reaction conditions and excellent functional-group compatibility and delivers the desired lactam products in moderate to good yields, even on a gram scale. Mechanistic studies support a nonchain radical pathway, which involves the formation of a dppb-Br electron donor-acceptor complex, followed by radical addition and intramolecular cyclization. This work presents a practical and environmentally friendly strategy for the construction of valuable fluorinated lactam frameworks.

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Cite This Study

Wang et al. (2026) studied this question.

synapsesocial.com/papers/69c4cc37fdc3bde448917765https://doi.org/10.1021/acs.orglett.6c00675
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