Nitrogen-centered radical-mediated α-sulfonimidation of ketones

An efficient and practical strategy for a nitrogen-centered radical mediated alpha-sulfonimidation of carbonyl compounds is established. The ketone alpha-sulfonimidation was initiated by a benzenesulfonimide radical generated from NFSI under the catalytic reduction of TEMPO that enables the sulfonimidation of enol esters to alpha-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 alpha-sulfonimidation was easily realized when a bulky leaving group was employed in the complex natural products.

Automated summary

An efficient and practical strategy for the nitrogen-centered radical mediated alpha-sulfonimidation of carbonyl compounds has been established. This strategy enables the sulfonimidation of enol esters to alpha-sulfonimide ketones under ambient conditions, and offers a convenient method for reacting with a diverse range of aromatic and aliphatic ketones with multiple structures. Additionally, it allows for stereoselective alpha-sulfonimidation in complex natural products when a bulky leaving group is employed.