4.7 Article

Palladium-Catalyzed Ring-Opening Coupling of gem-Difluorocyclopropanes for the Construction of 2-Fluoroallylic Sulfones

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 21, Pages 13646-13654

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01897

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Funding

  1. National Program on Key Basic Research Project of China [2015CB910603-004]
  2. Chinese National NSF [81430080, 81773565]

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A Pd-catalyzed ring-opening sulfonylation of gem-difluorocyclopropanes is reported. This protocol involves C-C bond cleavage, beta-F elimination, and allylic coupling to form corresponding 2-fluoroallylic sulfones efficiently with Z-selectivity. Different substrates bearing diverse functional groups are tolerated. Moreover, this method is successfully used for the late-stage derivation of several bioactive molecules.

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