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Ruthenium(II)-Catalyzed α-Fluoroalkenylation of Oxime Ethers with gem-Difluorostyrenes via C-H Activation and C-F Cleavage.

Lili ZhangKezuan DengGaorong WuJinyue YangShibiao TangXiaopan FuCheng-Cai XiaYafei Ji
Published in: The Journal of organic chemistry (2020)
A novel route for ruthenium(II)-catalyzed α-fluoroalkenylation of oxime ethers with gem-difluorostyrenes via C-H activation and C-F cleavage has been developed for the first time. Notably, the alkenyl units of products exhibit exclusive Z-configuration. This reaction features a broad substrate scope and good functional group tolerance. A plausible reaction mechanism is confirmed by an available cycloruthenated intermediate. Besides, the O-methyl oximyl-directing group can be readily removed to access the α-fluoroalkenylated acetophenones.
Keyphrases
  • room temperature
  • electron transfer
  • ionic liquid