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Construction of α-Acyloxy Ketones via Photoredox-Catalyzed O–H Insertion of Sulfoxonium Ylides with Carboxylic Acids

Qing Sun, Altman Yuzhu Peng, Yujing Wang, Xiaoguang Bao

2023Organic Letters35 citationsDOI

Abstract

Herein, a photoredox-catalyzed insertion of sulfoxonium ylides with carboxylic acids was advanced under mild and simple conditions, offering a practical approach for preparing α-acyloxy ketones with a broad scope of carboxylic acids. A combined experimental and computational study suggests that this reaction proceeds via a stepwise proton-assisted electron transfer mechanism.

Topics & Concepts

ChemistryCatalysisScope (computer science)Carboxylic acidCombinatorial chemistryPhotoredox catalysisProtonOrganic chemistryPhotocatalysisQuantum mechanicsComputer scienceProgramming languagePhysicsCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions
Construction of α-Acyloxy Ketones via Photoredox-Catalyzed O–H Insertion of Sulfoxonium Ylides with Carboxylic Acids | Litcius