Synthesis of Stable Hypervalent Bromine(III) Complexes by Oxidation with Lewis Acids Containing -Hybridized Nitrogen.

Org Lett

Department of Organic and Medicinal Chemistry, Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

Published: November 2024

Stable hypervalent bromine(III) compounds were synthesized via aryl bromine oxidation with -hybridized nitrogen cations generated by oxime N-O bond cleavage in trifluoroacetic acid. The resulting intramolecular N-Br hypervalent bond is effectively stabilized by the planar xanthone structure. The structures and physicochemical properties of these λ-bromanes were characterized by X-ray crystallography, cyclic voltammetry, UV-vis spectroscopy, and computational analysis.

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http://dx.doi.org/10.1021/acs.orglett.4c03881DOI Listing

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