Taming Bromine Azide for Use in Organic Solvents─Radical Bromoazidations and Alcohol Oxidations

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Abstract

The formation of bromine azide from the bisazidobromate(I) anion or alternatively from Zhdankin’s reagent, using a phosphonium bromide salt as a common starting point, is reported. After homolytic cleavage in the presence of alkenes or alcohols either 1,2-functionalization or alternatively the selective oxidation of secondary alcohols in the presence of primary alcohols occur. The scopes and limitations of the use of BrN3 are covered.

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Schulz, G., George, V., Taser, D., & Kirschning, A. (2023). Taming Bromine Azide for Use in Organic Solvents─Radical Bromoazidations and Alcohol Oxidations. Journal of Organic Chemistry, 88(6), 3781–3786. https://doi.org/10.1021/acs.joc.2c03012

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