Mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: Revisiting TEMPO-assisted oxidations

The present work addresses the development of an eco-friendly and cost-efficient protocol for the oxidation of primary and secondary alcohols to the corresponding aldehydes and ketones by mechanical processing under air. Ball milling was shown to promote the quantitative conversion of a broad set of...

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Autores principales: Porcheddu, Andrea, Colacino, Evelina, Cravotto, Giancarlo, Delogu, Francesco, De Luca, Lidia
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5647725/
https://www.ncbi.nlm.nih.gov/pubmed/29062426
http://dx.doi.org/10.3762/bjoc.13.202
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author Porcheddu, Andrea
Colacino, Evelina
Cravotto, Giancarlo
Delogu, Francesco
De Luca, Lidia
author_facet Porcheddu, Andrea
Colacino, Evelina
Cravotto, Giancarlo
Delogu, Francesco
De Luca, Lidia
author_sort Porcheddu, Andrea
collection PubMed
description The present work addresses the development of an eco-friendly and cost-efficient protocol for the oxidation of primary and secondary alcohols to the corresponding aldehydes and ketones by mechanical processing under air. Ball milling was shown to promote the quantitative conversion of a broad set of alcohols into carbonyl compounds with no trace of an over-oxidation to carboxylic acids. The mechanochemical reaction exhibited higher yields and rates than the classical, homogeneous, TEMPO-based oxidation.
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spelling pubmed-56477252017-10-23 Mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: Revisiting TEMPO-assisted oxidations Porcheddu, Andrea Colacino, Evelina Cravotto, Giancarlo Delogu, Francesco De Luca, Lidia Beilstein J Org Chem Full Research Paper The present work addresses the development of an eco-friendly and cost-efficient protocol for the oxidation of primary and secondary alcohols to the corresponding aldehydes and ketones by mechanical processing under air. Ball milling was shown to promote the quantitative conversion of a broad set of alcohols into carbonyl compounds with no trace of an over-oxidation to carboxylic acids. The mechanochemical reaction exhibited higher yields and rates than the classical, homogeneous, TEMPO-based oxidation. Beilstein-Institut 2017-10-02 /pmc/articles/PMC5647725/ /pubmed/29062426 http://dx.doi.org/10.3762/bjoc.13.202 Text en Copyright © 2017, Porcheddu et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Porcheddu, Andrea
Colacino, Evelina
Cravotto, Giancarlo
Delogu, Francesco
De Luca, Lidia
Mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: Revisiting TEMPO-assisted oxidations
title Mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: Revisiting TEMPO-assisted oxidations
title_full Mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: Revisiting TEMPO-assisted oxidations
title_fullStr Mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: Revisiting TEMPO-assisted oxidations
title_full_unstemmed Mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: Revisiting TEMPO-assisted oxidations
title_short Mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: Revisiting TEMPO-assisted oxidations
title_sort mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: revisiting tempo-assisted oxidations
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5647725/
https://www.ncbi.nlm.nih.gov/pubmed/29062426
http://dx.doi.org/10.3762/bjoc.13.202
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