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

Abstract

AbstractA 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.