Phenyliodonium diacetate mediated direct synthesis of benzonitriles from styrenes through oxidative cleavage of C═C bonds.

A metal-free PhI(OAc)2 mediated nitrogenation of alkenes through C═C bond cleavage using inorganic ammonia salt as nitrogen source under mild conditions was developed, affording nitriles in moderate to good yields. The advantages of this reaction are mild reaction conditions, operational simplicity, and use of an ammonium salt as nitrogen source. Based upon experimental observations, a plausible reaction mechanism is proposed.