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Single C(sp3)-F Bond Activation in a CF3 Group: Ipso-Defluorooxylation of (Trifluoromethyl)alkenes with Oximes.

Hao ZengChuanle ZhuHuan-Feng Jiang
Published in: Organic letters (2019)
The first defluorinative ipso-functionalization reaction of (trifluoromethyl)alkenes is reported. This exclusively regioselective ipso-defluorooxylation of (trifluoromethyl)alkenes with oximes affords various attractive O-(1,1-difluoroallyl)oxime ethers efficiently via a chemoselective single C(sp3)-F bond activation in the CF3 group. Primary mechanism studies indicated an anionic SN2-type substitution pathway might be involved in this transformation.
Keyphrases
  • cystic fibrosis
  • electron transfer