Angewandte Chemie, Год журнала: 2023, Номер 135(46)

Опубликована: Окт. 2, 2023

Abstract This research explores the enantioselective hydrosulfonylation of various α,β‐unsaturated carbonyl compounds via use visible light and redox‐active chiral Ni‐catalysis, facilitating synthesis enantioenriched α‐chiral sulfones with remarkable enantioselectivity (exceeding 99 % ee). A significant challenge entails enhancing reactivity between metal‐coordinated moderate electrophilic sulfonyl radicals, aiming to minimize background reactions. The success our approach stems from two distinctive attributes: 1) Cl‐atom abstraction employed for radical generation chlorides, 2) single‐electron reduction produce a key enolate Ni‐complex. latter process appears enhance feasibility radical's addition electron‐rich radical. An in‐depth investigation into reaction mechanism, supported by both experimental observations theoretical analysis, offers insight intricate process. Moreover, versatility methodology is highlighted through its successful application in late‐stage functionalization complex bioactive molecules, demonstrating practicality as strategy producing sulfones.

Язык: Английский