Photoredox-Catalyzed Ring-Opening Addition Reaction between Benzyl Bromides and Cyclic Ethers

Abstract

A novel nucleophilic reaction between cyclic ethers and benzyl bromides is achieved under photoredox catalysis. The reaction proceeds through a single-electron-transfer (SET) pathway rather than a common S_N2 mechanism. By two steps of reduction and oxidation, a benzyl bromide heterolyzes to give a carbocation and bromide ion under mild conditions, and then a cyclic ether captures both the carbo­cation and bromide ion to afford the addition product.

Key words

photoredox catalysis - carbocation - cyclic ether - benzyl bromide - ring-cleavage addition reaction - fluorine

Publication History

Received: 21 September 2021

Accepted: 18 October 2021

Accepted Manuscript online:
18 October 2021

Article published online:
09 December 2021

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