Palladium-catalyzed carbomonofluoromethylation of unactivated alkenes: rapid access to γ-monofluoromethyl carboxylic acid derivatives

Herein, we report a palladium-catalyzed regioselective carbomonofluoromethylation of unactivated alkenes. The reaction uses easily available fluorobis(phenylsulfonyl)methane (FBSM) as a fluoromethylating reagent, and proceeds smoothly with a wide variety of carbon electrophiles, including (hetero)aryl iodides, styrenyl iodides and TIPSBr. A range of remote gamma-CH2F/CD2F carboxylic acid derivatives were constructed rapidly after a simple reductive desulfonylation step. The reaction features high regioselectivity, mild and simple reaction conditions and a broad substrate scope, and is easy to scale up. Palladium-catalyzed regioselective carbomonofluoromethylation of unactivated alkenes for rapid access to gamma-monofluoromethyl carboxylic acid derivatives is described.