Litcius/Paper detail

Visible-Light-Driven Organocatalytic Alkoxylation of Benzylic C–H Bonds

Chunbo Bo, Fei Chen, Qingqing Bu, Zhi‐Hong Du, Min Li, Bin Dai, Ning Liu

2023The Journal of Organic Chemistry13 citationsDOI

Abstract

A variety of strategies for direct alkoxylation of the benzyl C–H bond have been developed toward the construction of benzyl ethers. The light-induced benzyl C–H bond alkoxylation provides an alternative strategy for the synthesis of these important intermediates. The photocatalyzed alkoxylation of the benzyl C–H bond has dominated by metal-catalyzed methods. Herein, we reported a light-driven organocatalytic approach for alkoxylation of the benzyl C–H bond by the use of 9,10-dibromoanthracene as a photocatalyst and employing N -fluorobenzenesulfonimide as an oxidant. This reaction proceeds at room temperature and is capable of converting a variety of alkyl biphenyl and coupling partners, including a variety of alcohol and carboxylic acid, as well as peroxide, to the desired products under 400 nm light irradiation.

Topics & Concepts

PhotocatalysisChemistryBenzyl alcoholCatalysisPhotoredox catalysisPhotochemistryVisible spectrumPeroxideAlkylBiphenylCombinatorial chemistryOrganic chemistryMedicinal chemistryMaterials scienceOptoelectronicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions