4.7 Article

Copper-Catalyzed Aminodifluoroalkylation of Alkenes with -Bromodifluoroacetamides: Synthesis of 3,3-Difluoropyrrolidin-2-ones

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 18, Pages 3114-3119

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700559

Keywords

Alkenes; copper; radical reactions; aminodifluoroalkylation; fluorinated nitrogen-containing heterocycles

Funding

  1. Henan Province Key Laboratory of New Opto-Electronic Functional Materials
  2. Science & Technology Foundation of Henan Province
  3. National NSF of China [21372041]
  4. Jilin Province Key Laboratory of Organic Functional Molecular Design Synthesis [130028651]

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Copper-catalyzed external-oxidant-free regioselective aminodifluoroalkylation of alkenes with readily available -bromodifluoroacetamides was realized. This reaction exhibits good functional group tolerance with respect to alkenes and -bromodifluoroacetamides in affording 3,3-difluoropyrrolidin-2-ones. A mechanism involving copper-catalyzed generation of a difluoroalkyl radical is proposed.

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