Selenium‐Catalyzed Electrophilic Cascade Reactions of Vinylarenes with N‐Fluorobenzenesulfonimide: A Novel Strategy for the Synthesis of β‐Keto Sulfones

Abstract

A selenium‐catalyzed electrophilic cascade reaction of vinylarenes with N‐fluorobenzenesulfonimide for the efficient synthesis of important β‐keto sulfones via a single operation is developed. The reactions of vinylarenes bearing electron‐withdrawing groups and electron‐donating groups proceeded smoothly in the air and gave products in up to 94% yield. Mechanistic studies suggest that vinyl amines generated by oxidative amination of vinylarenes are the intermediates, the cleavage of N‐S bond and the recombination of sulfonyl radical lead to 1,3‐migration of sulfonyl, and hydrolysis affords the products β‐keto sulfones.