Electrochemical Synthesis of Cyclic Biaryl λ3-Bromanes from 2,2’-Dibromobiphenyls

Submitting author affiliation:
Latvian Institute of Organic Synthesis, Riga, Latvia

Beilstein Arch. 2024, 202468. https://doi.org/10.3762/bxiv.2024.68.v1

Published 22 Nov 2024

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Abstract

The remarkable nucleofugality of diarylbromonium species renders them particularly suitable for 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 an access to a range of symmetrically and non-symmetrically substituted cyclic biaryl λ3-bromanes in moderate yields.

Keywords: Hypervalent bromine; electrochemistry; cyclic biaryl λ3-bromane; anodic oxidation; cyclic voltammetry

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Savkins, A.; Sokolovs, I. Beilstein Arch. 2024, 202468. doi:10.3762/bxiv.2024.68.v1

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