Metal-free C(sp2)-H perfluoroalkylsulfonylation and configuration inversion: Stereoselective synthesis of α-perfluoroalkylsulfonyl E-enaminones

The perfluoroalkylsulfonylation (CF3SO2, C2F5SO2 and CHF2SO2) in the enaminone C-H bonds has been developed simply via the promotion of molecular iodine by using stable and cheap sodium perfluoroalkyl sulfinates as coupling partners. The stereoselective synthesis of E-configurated alpha-perfluoroalkylsulfonyl enaminones has been realized via unprecedented C-H bond elaboration and C= C double bond configuration inversion by free radical process. (C) 2021 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

Automated summary

The perfluoroalkylsulfonylation in enaminone C-H bonds has been achieved by using molecular iodine promotion and stable, inexpensive sodium perfluoroalkyl sulfinates as coupling partners, leading to the stereoselective synthesis of E-configurated alpha-perfluoroalkylsulfonyl enaminones.