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

Cuiwen Kuang; Chuanfa Ni; Yucheng Gu; Jinbo Hu

doi:10.1055/a-1671-6856

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(05): 1272-1286
DOI: 10.1055/a-1671-6856

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

Autor*innen

Cuiwen Kuang

^aKey Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Shanghai 200032, P. R. of China
Chuanfa Ni

^aKey Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Shanghai 200032, P. R. of China
Yucheng Gu

^bSyngenta, Jealott’s Hill International Research Centre, Bracknell, Berkshire RG42 6EY, U.K.
Jinbo Hu ∗

^aKey Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Shanghai 200032, P. R. of China

Abstract

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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

Volltext

Referenzen

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Zusatzmaterial

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