Photocatalyzed Cyanodifluoromethylation of Alkenes.

Difluoromethylation is a straightforward and widely applied strategy used to incorporate HCF2 into organic molecules. In contrast, cyanation reagents are typically volatile or highly toxic, or they require harsh reaction conditions. Incorporation of both CN and HCF2 into organic molecules, such as alkenes, is a worthwhile but challenging task. A method for photocatalyzed cyanodifluoromethylation of alkenes has been developed, which employs a Ph3 P+ CF2 CO2 - /NaNH2 (or NH3 ) reagent system. Ph3 P+ CF2 CO2 - functions as both the HCF2 and CN carbon source. A cyanide anion is generated in situ under mild conditions, thereby avoiding the use of toxic cyanation reagents. The photocatalytic method permits cyanodifluoromethylation of a range of alkenes under mild room temperature conditions. The CN group within the products may be further derivatized by standard methods.