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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Main Authors:	Andrea Porcheddu, Evelina Colacino, Giancarlo Cravotto, Francesco Delogu, Lidia De Luca
Format:	Article
Language:	English
Published:	Beilstein-Institut 2017-10-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	aldehydes ball milling ketones mechanochemistry oxidation reactions TEMPO
Online Access:	https://doi.org/10.3762/bjoc.13.202

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spelling	doaj-b383cf80aac94e6dbf07828337b18ef02021-02-02T00:18:41ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972017-10-011312049205510.3762/bjoc.13.2021860-5397-13-202Mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: Revisiting TEMPO-assisted oxidationsAndrea Porcheddu0Evelina Colacino1Giancarlo Cravotto2Francesco Delogu3Lidia De Luca4Dipartimento di Scienze Chimiche e Geologiche, Università degli Studi di Cagliari, Cittadella Universitaria, SS 554 bivio per Sestu, 09028 Monserrato (Ca), ItalyDipartimento di Scienze Chimiche e Geologiche, Università degli Studi di Cagliari, Cittadella Universitaria, SS 554 bivio per Sestu, 09028 Monserrato (Ca), ItalyDipartimento di Scienza e Tecnologia del Farmaco, University of Turin, Via P. Giuria, 9, 10125 Turin, ItalyDipartimento di Ingegneria Meccanica, Chimica e dei Materiali, Università degli Studi di Cagliari, via Marengo 3, 09123 Cagliari, ItalyDipartimento di Chimica e Farmacia, Università degli Studi di Sassari, via Vienna 2, 07100 Sassari, ItalyThe 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.https://doi.org/10.3762/bjoc.13.202aldehydesball millingketonesmechanochemistryoxidation reactionsTEMPO
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Andrea Porcheddu Evelina Colacino Giancarlo Cravotto Francesco Delogu Lidia De Luca
spellingShingle	Andrea Porcheddu Evelina Colacino Giancarlo Cravotto Francesco Delogu Lidia De Luca Mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: Revisiting TEMPO-assisted oxidations Beilstein Journal of Organic Chemistry aldehydes ball milling ketones mechanochemistry oxidation reactions TEMPO
author_facet	Andrea Porcheddu Evelina Colacino Giancarlo Cravotto Francesco Delogu Lidia De Luca
author_sort	Andrea Porcheddu
title	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_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_sort	mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: revisiting tempo-assisted oxidations
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2017-10-01
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.
topic	aldehydes ball milling ketones mechanochemistry oxidation reactions TEMPO
url	https://doi.org/10.3762/bjoc.13.202
work_keys_str_mv	AT andreaporcheddu mechanicallyinducedoxidationofalcoholstoaldehydesandketonesinambientairrevisitingtempoassistedoxidations AT evelinacolacino mechanicallyinducedoxidationofalcoholstoaldehydesandketonesinambientairrevisitingtempoassistedoxidations AT giancarlocravotto mechanicallyinducedoxidationofalcoholstoaldehydesandketonesinambientairrevisitingtempoassistedoxidations AT francescodelogu mechanicallyinducedoxidationofalcoholstoaldehydesandketonesinambientairrevisitingtempoassistedoxidations AT lidiadeluca mechanicallyinducedoxidationofalcoholstoaldehydesandketonesinambientairrevisitingtempoassistedoxidations
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Mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: Revisiting TEMPO-assisted oxidations

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