Electrochemical Synthesis of Dimeric λ3-Bromane: Platform for Hypervalent Bromine(III) Compounds

Igors Sokolovs; Edgars Suna

doi:10.1021/acs.orglett.3c00405

Electrochemical Synthesis of Dimeric λ³-Bromane: Platform for Hypervalent Bromine(III) Compounds

Org Lett. 2023 Mar 31;25(12):2047-2052. doi: 10.1021/acs.orglett.3c00405. Epub 2023 Mar 21.

Authors

Igors Sokolovs¹, Edgars Suna^{1

2}

Affiliations

¹ Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006 Riga, Latvia.
² Department of Chemistry, University of Latvia, Jelgavas 1, LV-1004 Riga, Latvia.

Abstract

A straightforward and scalable approach to a previously unreported class of cyclic hypervalent Br(III) species capitalizes on the anodic oxidation of aryl bromide to dimeric benzbromoxole that serves as a versatile platform to access a range of structurally diverse Br(III) congeners such as acetoxy-, alkoxy-, and ethynyl-λ³-bromanes as well as diaryl-λ³-bromanes. The synthetic utility of dimeric λ³-bromane is exemplified by photoinduced Minisci-type heteroarylation reactions and benzylic oxidation.