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A H(2)O(2)/HBr system – several directions but one choice: oxidation–bromination of secondary alcohols into mono- or dibromo ketones

In this work we found that a H(2)O(2)–HBr(aq) system allows synthesis of α-monobromo ketones and α,α′-dibromo ketones from aliphatic and secondary benzylic alcohols with yields up to 91%. It is possible to selectively direct the process toward the formation of mono- or dibromo ketones by varying the...

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Autores principales: Nikishin, Gennady I., Kapustina, Nadezhda I., Sokova, Liubov L., Bityukov, Oleg V., Terent'ev, Alexander O.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9084404/
https://www.ncbi.nlm.nih.gov/pubmed/35548402
http://dx.doi.org/10.1039/c8ra04885a
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author Nikishin, Gennady I.
Kapustina, Nadezhda I.
Sokova, Liubov L.
Bityukov, Oleg V.
Terent'ev, Alexander O.
author_facet Nikishin, Gennady I.
Kapustina, Nadezhda I.
Sokova, Liubov L.
Bityukov, Oleg V.
Terent'ev, Alexander O.
author_sort Nikishin, Gennady I.
collection PubMed
description In this work we found that a H(2)O(2)–HBr(aq) system allows synthesis of α-monobromo ketones and α,α′-dibromo ketones from aliphatic and secondary benzylic alcohols with yields up to 91%. It is possible to selectively direct the process toward the formation of mono- or dibromo ketones by varying the amount of hydrogen peroxide and hydrobromic acid. The convenience of application, simple equipment, multifaceted reactivity, and compliance with green chemistry principles make the application of the H(2)O(2)–HBr(aq) system very attractive in laboratories and industry. The proposed oxidation–bromination process is selective in spite of known properties of ketones to be oxidized by the Baeyer–Villiger reaction or peroxidated with the formation of compounds with the O–O moiety in the presence of hydrogen peroxide and Bronsted acids.
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spelling pubmed-90844042022-05-10 A H(2)O(2)/HBr system – several directions but one choice: oxidation–bromination of secondary alcohols into mono- or dibromo ketones Nikishin, Gennady I. Kapustina, Nadezhda I. Sokova, Liubov L. Bityukov, Oleg V. Terent'ev, Alexander O. RSC Adv Chemistry In this work we found that a H(2)O(2)–HBr(aq) system allows synthesis of α-monobromo ketones and α,α′-dibromo ketones from aliphatic and secondary benzylic alcohols with yields up to 91%. It is possible to selectively direct the process toward the formation of mono- or dibromo ketones by varying the amount of hydrogen peroxide and hydrobromic acid. The convenience of application, simple equipment, multifaceted reactivity, and compliance with green chemistry principles make the application of the H(2)O(2)–HBr(aq) system very attractive in laboratories and industry. The proposed oxidation–bromination process is selective in spite of known properties of ketones to be oxidized by the Baeyer–Villiger reaction or peroxidated with the formation of compounds with the O–O moiety in the presence of hydrogen peroxide and Bronsted acids. The Royal Society of Chemistry 2018-08-10 /pmc/articles/PMC9084404/ /pubmed/35548402 http://dx.doi.org/10.1039/c8ra04885a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Nikishin, Gennady I.
Kapustina, Nadezhda I.
Sokova, Liubov L.
Bityukov, Oleg V.
Terent'ev, Alexander O.
A H(2)O(2)/HBr system – several directions but one choice: oxidation–bromination of secondary alcohols into mono- or dibromo ketones
title A H(2)O(2)/HBr system – several directions but one choice: oxidation–bromination of secondary alcohols into mono- or dibromo ketones
title_full A H(2)O(2)/HBr system – several directions but one choice: oxidation–bromination of secondary alcohols into mono- or dibromo ketones
title_fullStr A H(2)O(2)/HBr system – several directions but one choice: oxidation–bromination of secondary alcohols into mono- or dibromo ketones
title_full_unstemmed A H(2)O(2)/HBr system – several directions but one choice: oxidation–bromination of secondary alcohols into mono- or dibromo ketones
title_short A H(2)O(2)/HBr system – several directions but one choice: oxidation–bromination of secondary alcohols into mono- or dibromo ketones
title_sort h(2)o(2)/hbr system – several directions but one choice: oxidation–bromination of secondary alcohols into mono- or dibromo ketones
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9084404/
https://www.ncbi.nlm.nih.gov/pubmed/35548402
http://dx.doi.org/10.1039/c8ra04885a
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