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

Cuiwen Kuang
a   Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Shanghai 200032, P. R. of China
,
Chuanfa Ni
a   Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Shanghai 200032, P. R. of China
,
b   Syngenta, Jealott’s Hill International Research Centre, Bracknell, Berkshire RG42 6EY, U.K.
,
Jinbo Hu
a   Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Shanghai 200032, P. R. of China
› Institutsangaben
This work was supported by the National Key Research and Development Program of China (2016YFB0101200), the National Natural Science Foundation of China (21632009), the Key Programs of the Chinese Academy of Sciences (KGZD-EW-T08), the Key Research Program of Frontier Sciences of CAS (QYZDJ-SSW-SLH049).


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 SN2 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.

Supporting Information



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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