A radical anti-Markovnikov addition of alkyl nitriles to simple alkenes via selective sp(3) C-H bond functionalization

An efficient hydrocyanoalkylation of unactivated alkenes with alkyl nitriles was developed. Through this free-radical-initiated selective activation of the alpha-C(sp(3))-H bond of acetonitriles, an anti-Markovnikov addition of an alpha-cyano C-centered radical to olefins has been achieved, which allows a facile and convenient access to functionalized nitriles in large scales.