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

Chunbo Bo, Fei Chen, Qingqing Bu, Zhi-Hong Du, Min Li, Bin Dai*, and Ning Liu*. J. Org. Chem. 2023, 88, 3532–3538.

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.