Base-Promoted N-α- C–H Alkylation of Aliphatic Amines via Tandem SET/1,5-HAT Processes

A tandem SET/1,5-HAT reaction of 2-iodobenzamides and N -benzhydryl imines for the synthesis of 1,2-diamine derivatives is described. Using super electron donor (SED) 2-azaallyl anions, single-electron transfer (SET) generates an aryl radical. A hydrogen atom transfer (HAT) from N-α- C(sp 3 )–H to the aryl radical generates alkyl radicals, which is followed by coupling with 2-azaallyl radicals to produce diamine derivatives.