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

Publikationsverlauf

Eingereicht: 21. September 2021

Angenommen: 18. Oktober 2021

Accepted Manuscript online:
18. Oktober 2021

Artikel online veröffentlicht:
09. Dezember 2021

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