One and two electron chemistry of 2-azaallyl anions

Our team has been interested in the fascinating chemistry of 2-azaallyl anions, which involves both SET reactions and two electron processes.  We have found that 2-azaallyl anion undergo cross-coupling with aryl halides and hindered alkyl iodides via SET reactions followed by radical-radical coupling in the absence of transition metal catalysts.  This mode of reactivity has been used to prepare valuable heterocycles.  Cross dehydrogenative coupling reactions in the absence of transition metals can also be performed, as can a variety of transition metal catalyzed coupling processes.