Electrochemical synthesis of cyclic biaryl λ3-bromanes from 2,2’-dibromobiphenyls

The remarkable nucleofugality of bromoarenes in diarylbromonium species renders them particularly suitable for the generation of arynes for subsequent use in a wide range of synthetic applications. The common approach to generate cyclic biaryl λ3-bromanes is based on thermal decomposition of hazardo...

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Bibliographic Details
Main Authors: Andrejs Savkins, Igors Sokolovs
Format: Article
Language:English
Published: Beilstein-Institut 2025-02-01
Series:Beilstein Journal of Organic Chemistry
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Online Access:https://doi.org/10.3762/bjoc.21.32
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Summary:The remarkable nucleofugality of bromoarenes in diarylbromonium species renders them particularly suitable for the generation of arynes for subsequent use in a wide range of synthetic applications. The common approach to generate cyclic biaryl λ3-bromanes is based on thermal decomposition of hazardous diazonium salts. Herein, we disclose a mild and straightforward approach to diarylbromonium species by direct anodic oxidation of 2,2'-dibromo-1,1'-biphenyl. The electrochemical method provides access to a range of symmetrically and non-symmetrically substituted cyclic biaryl λ3-bromanes in moderate yields.
ISSN:1860-5397