Enantioselective C(sp 3 )–C(sp 3 ) Cross-Coupling between Oxacycles and Alkylsilyl Peroxides via a Dual Photoredox/Nickel Catalytic System
Abstract
Enantioselective C(sp 3 )–H functionalization offers a powerful approach to the streamlined synthesis of high-value chiral molecules. However, achieving the direct catalytic construction of asymmetric C(sp 3 )–C(sp 3 ) bonds from hydrocarbon substrates without directing groups remains a challenge. Herein, we outline the development of an enantioselective C(sp 3 )–C(sp 3 ) cross-coupling between oxacycles and alkylsilyl peroxides via a dual photoredox-nickel catalytic system. Unlike other radical precursors, the reactivity of alkylsilyl peroxides can be finely tuned through variation of the silicon substituents. A chiral nickel catalyst promotes enantioselective alkyl–alkyl radical cross-coupling efficiently, affording a series of enantioenriched oxacyclic compounds. A plausible reaction mechanism is proposed based on the experimental observations.
Fields of Study & Subjects
Radical Photochemical Reactions
Catalytic C–H Functionalization Methods
Cyclopropane Reaction Mechanisms
Publication details
- Journal / source
- ACS Catalysis
- Publisher
- American Chemical Society (ACS)
- Volume
- 16
- Issue
- 6
- Pages
- 5466–5473
- Publication date
- 4 March 2026
- Language
- EN