Silver-Catalyzed Anti-Markovnikov Hydroxyfluorination of Styrenes

A silver-catalyzed radical hydroxyfluorination of styrenes with Selectfluor and H2O has been explored with exclusive anti-Markovnikov-type regioselectivity, thus affording vicinal fluorohydrins with regioselectivities opposite that of noncatalyzed processes. This reaction is operationally simple, scalable under mild conditions. The mechanism studies and DFT calculations revealed that the reaction go through a radical mechanism.