Palladium-catalyzed cascade 5-exo-trig radical cyclization/aromatic C-H alkylation with unactivated alkyl iodides.

A novel and convenient palladium-catalyzed cascade 5-exo-trig radical cyclization/aromatic C-H alkylation with unactivated alkyl iodides has been described. This strategy provides an efficient access to a variety of 3a-methyl-1,2,3,3a,4,8b-hexahydroindeno[1,2-b]pyrrole derivatives, which facilitate access to a series of medically important heterocyclic bioactive molecules. This protocol involves mild catalytic reaction conditions and shows high functional group tolerance with high stereoselectivity. Mechanistic investigations reveal that an alkyl radical pathway is involved in this reaction.