Litcius/Paper detail

Stereoselective Three-Component Allylic Alkylation Enabled by Dual Photoredox/Ni Catalysis

Qian Zeng, Fengyun Gao, Jordi Benet‐Buchholz, Arjan W. Kleij

2023ACS Catalysis22 citationsDOI

Abstract

A modular and practical approach has been developed for the stereoselective formation of elaborate allylic alcohols through a three-component reaction (3CR) between vinyl cyclic carbonates, olefins, and various radical precursors using dual photoredox/Ni catalysis. The developed process expands the potential of radical-based allylic alkylation to multicomponent approaches under high regio- and stereocontrol with ample variation of the individual reagents and offers access to compounds featuring sterically congested and functionalized quaternary carbon centers. The catalytic protocol can be expanded to other allylic precursors, and the stereoselectivity is reversed by simply changing the photocatalyst.

Topics & Concepts

StereoselectivityAllylic rearrangementChemistryCatalysisTsuji–Trost reactionAlkylationSteric effectsCombinatorial chemistryReagentPhotoredox catalysisOrganic chemistryPhotocatalysisRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques