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Aromatization as an Impetus to Harness Ketones for Metallaphotoredox-Catalyzed Benzoylation/Benzylation of (Hetero)arenes

Shao‐Chi Lee, Liyun Li, Zong‐Nan Tsai, Yi-Hsin Lee, Yong‐Ting Tsao, Pin-Gong Huang, Cheng-Ku Cheng, Heng-Bo Lin, Tingwei Chen, Chung-Hsin Yang, Cheng‐chau Chiu, Hsuan‐Hung Liao

2021Organic Letters57 citationsDOI

Abstract

Herein we report ketones as feedstock materials in radical cross-coupling reactions under Ni/photoredox dual catalysis. In this approach, simple condensation first converts ketones into prearomatic intermediates that then act as activated radical sources for cross-coupling with aryl halides. Our strategy enables the direct benzylation/benzoylation of (hetero)arenes under mild reaction conditions with high functional group tolerance.

Topics & Concepts

ChemistryAromatizationArylCatalysisHalideOrganic chemistryFunctional groupCombinatorial chemistryCoupling reactionAlkylPolymerRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
Aromatization as an Impetus to Harness Ketones for Metallaphotoredox-Catalyzed Benzoylation/Benzylation of (Hetero)arenes | Litcius