4.8 Article

Nickel-Catalyzed Defluorinative Reductive Cross-Coupling of gem-Difluoroalkenes with Unactivated Secondary and Tertiary Alkyl Halides

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 36, Pages 12632-12637

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b06469

Keywords

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Funding

  1. National Natural Science Foundation of China [21325208, 21572212, 21502184, 21732006, 21702200]
  2. Ministry of Science and Technology of China [2017YFA0303500]
  3. Chinese Academy of Science [XDB20000000]
  4. Key Technologies R&D Programme of Anhui Province [1604a0702027]
  5. FRFCU
  6. PCSIRT
  7. China Postdoctoral Science Foundation [2016M600482, 2017T100448]

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Herein, we described a nickel-catalyzed monofluoroalkenylation through defluorinative reductive cross-coupling of gem-difluoroalkenes with alkyl halides. Key to the success of this strategy is the combination of C- F cleavage with alkyl halides activation. This reaction enables the convenient synthesis of a large variety of functionalized monofluoroalkenes under mild reaction conditions with broad functional group compatibility and excellent Z-selectivity. The combination of Ni catalysis with (Bpin)(2)/K3PO4 as terminal reductant promoted the efficient C(sp(2))-C(sp(3)) formation especially the generation of all-carbon quatemary centers with high chemoselectivity.

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