Electrochemically Induced Regio- and Stereoselective (E)-beta-C(sp(2))-H Trifluoromethylation and Arylsulfonylation of Enamides

Herein, we disclosed an electrochemically induced method for the regio- and stereoselective (E)-beta-C(sp(2))-H trifluoromethylation of enamides by employing readily available and inexpensive Langlois' reagent (CF3SO2Na). Preliminary mechanistic studies indicate the involvement of free radicals in the process. The exogenous oxidant-free reaction proceeds in an undivided electrochemical cell under mild conditions and allows for the accomplishment of the trifluoromethylation products with exclusive E-selective control. The methodology is featured by catalyst-free, simple setup, and broad substrate scopes of enamides with good functional group tolerance. Using ArSO2Na as the coupling partner, the corresponding (E)-beta-C(sp(2))-H arylsulfonylated enamides products are obtained under standard reaction conditions.

Automated summary

In this study, an electrochemically induced method for regio- and stereoselective (E)-beta-C(sp(2))-H trifluoromethylation of enamides was disclosed. The method features catalyst-free, simple setup, and broad substrate scopes, allowing for the synthesis of products with exclusive E-selective control under mild conditions.