Nitrogen-centered radical-mediated α-sulfonimidation of ketones

Abstract

An efficient and practical strategy for a nitrogen-centered radical mediated α-sulfonimidation of carbonyl compounds is established. The ketone α-sulfonimidation was initiated by a benzenesulfonimide radical generated from NFSI under the catalytic reduction of TEMPO that enables the sulfonimidation of enol esters to α-sulfonimide ketones under ambient conditions. This strategy conveniently engaged a diverse range of aromatic and aliphatic ketones with multiple structures. We also discovered that the stereoselective α-sulfonimidation was easily realized when a bulky leaving group was employed in the complex natural products.