Difluoromethylated Difunctionalization of Alkenes under Visible Light.

Difluoromethylated compounds usually act as bioisosteres for alcohol functional groups and show unique physicochemical and biological properties. The cyano-difluoromethylation of alkenes using 5-((difluoromethyl)sulfonyl)-1-phenyl-1 H -tetrazole as a CF 2 H radical difluoromethyl precursor was developed to afford nitriles including a CF 2 H group. A low-cost, stable, easily handled 5-((difluoromethyl)sulfonyl)-1-methyl- 1H -tetrazole (DFSMT) was synthesized and applied as the radical CF 2 H reagent. Using DFSMT as the radical CF 2 H precursor, the oxyl-difluoromethylation of alkenes was developed to obtain difluoromethylated ether products. All of the reactions showed good functional group tolerability. Initial mechanistic experiments indicated that the CF 2 H radical was involved as the key active intermediate.