Cobalt-Catalyzed 1,4-Aryl Migration/Desulfonylation Cascade: Synthesis of α-Aryl Amides

A cobalt-catalyzed 1,4-aryl migration/disulfonylation cascade applied to alpha-bromo N-sulfonyl amides was developed. The reaction was highly chemoselective, allowing the preparation of alpha-aryl amides possessing a variety of functional groups. The method was used as the key step to synthesize an alkaloid, (+/-)-deoxyeseroline. Mechanistic investigations suggest a radical process.

Automated summary

A cobalt-catalyzed reaction method with high chemoselectivity was developed for the preparation of alpha-aryl amides with various functional groups. This method was successfully applied to the synthesis of alkaloids. Mechanistic studies suggest a radical process.