Synthesis of Bicyclic Nitrogen Compounds via Tandem Intramolecular Heck Cyclization and Subsequent Trapping of Intermediate π-Allylpalladium Complexes

Intramolecular palladium-mediated three-component cyclizations of substrates containing vinyl halide, olefin, and sulfonamide moieties to generate a diverse group of nitrogen heterocycles have been developed. The methodology has been applied to construction of both fused and bridged bicyclic systems. The strategy can also be used for spirocyclizations. This chemistry involves regiospecific generation of π-allylpalladium complexes via Heck reactions of vinyl halides and simple olefins, followed by nucleophilic addition of sulfonamide anions to these intermediates.