Selective C(sp(3))−H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow

A mild and selective C(sp(3))−H aerobic oxidation enabled by decatungstate photocatalysis has been developed. The reaction can be significantly improved in a microflow reactor enabling the safe use of oxygen and enhanced irradiation of the reaction mixture. Our method allows for the oxidation of bot...

Descripción completa

Detalles Bibliográficos
Autores principales: Laudadio, Gabriele, Govaerts, Sebastian, Wang, Ying, Ravelli, Davide, Koolman, Hannes F., Fagnoni, Maurizio, Djuric, Stevan W., Noël, Timothy
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5900731/
https://www.ncbi.nlm.nih.gov/pubmed/29451725
http://dx.doi.org/10.1002/anie.201800818
_version_ 1783314472882929664
author Laudadio, Gabriele
Govaerts, Sebastian
Wang, Ying
Ravelli, Davide
Koolman, Hannes F.
Fagnoni, Maurizio
Djuric, Stevan W.
Noël, Timothy
author_facet Laudadio, Gabriele
Govaerts, Sebastian
Wang, Ying
Ravelli, Davide
Koolman, Hannes F.
Fagnoni, Maurizio
Djuric, Stevan W.
Noël, Timothy
author_sort Laudadio, Gabriele
collection PubMed
description A mild and selective C(sp(3))−H aerobic oxidation enabled by decatungstate photocatalysis has been developed. The reaction can be significantly improved in a microflow reactor enabling the safe use of oxygen and enhanced irradiation of the reaction mixture. Our method allows for the oxidation of both activated and unactivated C−H bonds (30 examples). The ability to selectively oxidize natural scaffolds, such as (−)‐ambroxide, pregnenolone acetate, (+)‐sclareolide, and artemisinin, exemplifies the utility of this new method.
format Online
Article
Text
id pubmed-5900731
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-59007312018-04-23 Selective C(sp(3))−H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow Laudadio, Gabriele Govaerts, Sebastian Wang, Ying Ravelli, Davide Koolman, Hannes F. Fagnoni, Maurizio Djuric, Stevan W. Noël, Timothy Angew Chem Int Ed Engl Communications A mild and selective C(sp(3))−H aerobic oxidation enabled by decatungstate photocatalysis has been developed. The reaction can be significantly improved in a microflow reactor enabling the safe use of oxygen and enhanced irradiation of the reaction mixture. Our method allows for the oxidation of both activated and unactivated C−H bonds (30 examples). The ability to selectively oxidize natural scaffolds, such as (−)‐ambroxide, pregnenolone acetate, (+)‐sclareolide, and artemisinin, exemplifies the utility of this new method. John Wiley and Sons Inc. 2018-03-12 2018-04-03 /pmc/articles/PMC5900731/ /pubmed/29451725 http://dx.doi.org/10.1002/anie.201800818 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Laudadio, Gabriele
Govaerts, Sebastian
Wang, Ying
Ravelli, Davide
Koolman, Hannes F.
Fagnoni, Maurizio
Djuric, Stevan W.
Noël, Timothy
Selective C(sp(3))−H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow
title Selective C(sp(3))−H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow
title_full Selective C(sp(3))−H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow
title_fullStr Selective C(sp(3))−H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow
title_full_unstemmed Selective C(sp(3))−H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow
title_short Selective C(sp(3))−H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow
title_sort selective c(sp(3))−h aerobic oxidation enabled by decatungstate photocatalysis in flow
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5900731/
https://www.ncbi.nlm.nih.gov/pubmed/29451725
http://dx.doi.org/10.1002/anie.201800818
work_keys_str_mv AT laudadiogabriele selectivecsp3haerobicoxidationenabledbydecatungstatephotocatalysisinflow
AT govaertssebastian selectivecsp3haerobicoxidationenabledbydecatungstatephotocatalysisinflow
AT wangying selectivecsp3haerobicoxidationenabledbydecatungstatephotocatalysisinflow
AT ravellidavide selectivecsp3haerobicoxidationenabledbydecatungstatephotocatalysisinflow
AT koolmanhannesf selectivecsp3haerobicoxidationenabledbydecatungstatephotocatalysisinflow
AT fagnonimaurizio selectivecsp3haerobicoxidationenabledbydecatungstatephotocatalysisinflow
AT djuricstevanw selectivecsp3haerobicoxidationenabledbydecatungstatephotocatalysisinflow
AT noeltimothy selectivecsp3haerobicoxidationenabledbydecatungstatephotocatalysisinflow

Ejemplares similares