Intramolecular arylcyanation of alkenes catalyzed by nickel/AlMe2CI

A catalyst system derived from nickel and cocatalytic AlMe2Cl effects the intramolecular arylcyanation of alkenes. The reaction takes place in an exclusive exo-dig manner to give a wide range of nitrites having a benzylic quaternary carbon in good yields. Detailed investigations are described on the scope and mechanism as well as preliminary results on the asymmetric version of the reaction to provide novel access to chiral quaternary stereocenters.