Cobalt-Catalyzed Synthesis of Alkenyl Heterocycles via Regioselective Intramolecular 1,4-Hydrofunctionalization of Dienes

We report a novel cobalt-catalyzed intramolecular 1,4-hydrofunctionalization of dienes. The reaction proceeds under mild conditions and is amenable to N- and O-nucleophiles. The protocol exhibits exclusive regioselectivity, yielding a number of different alkenyl heterocycles, including but not limited to dihydroisobenzofurans, isochromanes, tetrahydrofurans, morpholines, lactones, and isoindolines. Experimental studies were performed to offer some insight into the different mechanistic pathways and to rationalize the regio- and stereoselectivities of the reaction.