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

[Image: see text] 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 alter...

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Autores principales: Schulz, Göran, George, Vincent, Taser, Daghan, Kirschning, Andreas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10028602/
https://www.ncbi.nlm.nih.gov/pubmed/36821827
http://dx.doi.org/10.1021/acs.joc.2c03012
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author Schulz, Göran
George, Vincent
Taser, Daghan
Kirschning, Andreas
author_facet Schulz, Göran
George, Vincent
Taser, Daghan
Kirschning, Andreas
author_sort Schulz, Göran
collection PubMed
description [Image: see text] 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 BrN(3) are covered.
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spelling pubmed-100286022023-03-22 Taming Bromine Azide for Use in Organic Solvents—Radical Bromoazidations and Alcohol Oxidations Schulz, Göran George, Vincent Taser, Daghan Kirschning, Andreas J Org Chem [Image: see text] 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 BrN(3) are covered. American Chemical Society 2023-02-23 /pmc/articles/PMC10028602/ /pubmed/36821827 http://dx.doi.org/10.1021/acs.joc.2c03012 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Schulz, Göran
George, Vincent
Taser, Daghan
Kirschning, Andreas
Taming Bromine Azide for Use in Organic Solvents—Radical Bromoazidations and Alcohol Oxidations
title Taming Bromine Azide for Use in Organic Solvents—Radical Bromoazidations and Alcohol Oxidations
title_full Taming Bromine Azide for Use in Organic Solvents—Radical Bromoazidations and Alcohol Oxidations
title_fullStr Taming Bromine Azide for Use in Organic Solvents—Radical Bromoazidations and Alcohol Oxidations
title_full_unstemmed Taming Bromine Azide for Use in Organic Solvents—Radical Bromoazidations and Alcohol Oxidations
title_short Taming Bromine Azide for Use in Organic Solvents—Radical Bromoazidations and Alcohol Oxidations
title_sort taming bromine azide for use in organic solvents—radical bromoazidations and alcohol oxidations
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10028602/
https://www.ncbi.nlm.nih.gov/pubmed/36821827
http://dx.doi.org/10.1021/acs.joc.2c03012
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