Preparation of Annulated Nitrogen-Containing Heterocycles via a One-Pot Palladium-Catalyzed Alkylation/Direct Arylation Sequence

A palladium-catalyzed/norbornene-mediated sequential coupling reaction involving an aromatic sp2 C−H functionalization as the key step is described, in which an alkyl−aryl bond and an aryl−heteroaryl bond are formed in one pot. A variety of highly substituted six- and seven-membered annulated pyrroles and pyrazoles were synthesized in a one-step process in good yields from readily accessible N-bromoalkyl pyrroles or pyrazoles and aryl iodides.