Cobalt(III)-Catalyzed Regioselective [4 + 2]-Annulation of N-Chlorobenzamides with Substituted Alkenes.

Abstract

A Co(III)-catalyzed redox-neutral [4 + 2] annulation of N-chlorobenzamides/acrylamides with substituted alkenes at ambient temperature is demonstrated. Using this protocol, pharmaceutically important 3,4-dihydroisoquinolinone derivatives were synthesized in good yields. Intriguingly, the synthetically useful functional group of allylic coupling partners such as sulfonyl, carbonate, acetate, phosphate, amide, nitrile, and silane were retained in the final cyclized product. The present annulation reaction was compatible with various substituted benzamides and allylic coupling partners. To support the proposed reaction mechanism, competition experiments, deuterium labeling studies, and kinetic isotope effect studies were performed.