Transition-metal-free C(sp)-H/C(sp)-H dehydrogenative coupling of saturated heterocycles with -benzyl imines.

A unique C(sp)-H/C(sp)-H dehydrocoupling of -benzylimines with saturated heterocycles is described. Using super electron donor (SED) 2-azaallyl anions and aryl iodides as electron acceptors, single-electron-transfer (SET) generates an aryl radical. Hydrogen atom transfer (HAT) from saturated heterocycles or toluenes to the aryl radical generates alkyl radicals or benzylic radicals, respectively.