Synthesis of 1,3‐Dioxan‐2‐ones by Photo‐Aerobic Selenium‐π‐Acid Multicatalysis
An expedient method for the synthesis of cyclic carbonates from homoallylic carbonic acid esters by means of photo‐aerobic selenium‐π‐acid multicatalysis is reported. Until now, conceptually related methods commonly relied either on the stoichiometric addition of electrophiles onto the substrate...
Published in: | European Journal of Organic Chemistry |
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2022
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ftpubmed:oai:pubmedcentral.nih.gov:10108053 2023-06-11T04:10:54+02:00 Synthesis of 1,3‐Dioxan‐2‐ones by Photo‐Aerobic Selenium‐π‐Acid Multicatalysis Müller, Kilian A. Nagel, Carolin H. Breder, Alexander 2022-12-22 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10108053/ https://doi.org/10.1002/ejoc.202201180 en eng John Wiley and Sons Inc. http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10108053/ http://dx.doi.org/10.1002/ejoc.202201180 © 2022 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. European J Org Chem Research Articles Text 2022 ftpubmed https://doi.org/10.1002/ejoc.202201180 2023-04-23T00:50:59Z An expedient method for the synthesis of cyclic carbonates from homoallylic carbonic acid esters by means of photo‐aerobic selenium‐π‐acid multicatalysis is reported. Until now, conceptually related methods commonly relied either on the stoichiometric addition of electrophiles onto the substrate's alkene moiety or the presence of pre‐installed leaving groups in allylic position of said alkene to – in part, catalytically – initiate an intramolecular attack by an adjacent carbonic acid ester group. In sharp contrast, the current study shows that the C−C double bond of homoallylic carbonic acid esters can be directly activated by the catalytic interplay of a pyrylium dye and a diselane using ambient air as the sole oxidant and visible light as an energy source. Text Carbonic acid PubMed Central (PMC) European Journal of Organic Chemistry 26 2 |
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Research Articles |
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Research Articles Müller, Kilian A. Nagel, Carolin H. Breder, Alexander Synthesis of 1,3‐Dioxan‐2‐ones by Photo‐Aerobic Selenium‐π‐Acid Multicatalysis |
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Research Articles |
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An expedient method for the synthesis of cyclic carbonates from homoallylic carbonic acid esters by means of photo‐aerobic selenium‐π‐acid multicatalysis is reported. Until now, conceptually related methods commonly relied either on the stoichiometric addition of electrophiles onto the substrate's alkene moiety or the presence of pre‐installed leaving groups in allylic position of said alkene to – in part, catalytically – initiate an intramolecular attack by an adjacent carbonic acid ester group. In sharp contrast, the current study shows that the C−C double bond of homoallylic carbonic acid esters can be directly activated by the catalytic interplay of a pyrylium dye and a diselane using ambient air as the sole oxidant and visible light as an energy source. |
format |
Text |
author |
Müller, Kilian A. Nagel, Carolin H. Breder, Alexander |
author_facet |
Müller, Kilian A. Nagel, Carolin H. Breder, Alexander |
author_sort |
Müller, Kilian A. |
title |
Synthesis of 1,3‐Dioxan‐2‐ones by Photo‐Aerobic Selenium‐π‐Acid Multicatalysis |
title_short |
Synthesis of 1,3‐Dioxan‐2‐ones by Photo‐Aerobic Selenium‐π‐Acid Multicatalysis |
title_full |
Synthesis of 1,3‐Dioxan‐2‐ones by Photo‐Aerobic Selenium‐π‐Acid Multicatalysis |
title_fullStr |
Synthesis of 1,3‐Dioxan‐2‐ones by Photo‐Aerobic Selenium‐π‐Acid Multicatalysis |
title_full_unstemmed |
Synthesis of 1,3‐Dioxan‐2‐ones by Photo‐Aerobic Selenium‐π‐Acid Multicatalysis |
title_sort |
synthesis of 1,3‐dioxan‐2‐ones by photo‐aerobic selenium‐π‐acid multicatalysis |
publisher |
John Wiley and Sons Inc. |
publishDate |
2022 |
url |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10108053/ https://doi.org/10.1002/ejoc.202201180 |
genre |
Carbonic acid |
genre_facet |
Carbonic acid |
op_source |
European J Org Chem |
op_relation |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10108053/ http://dx.doi.org/10.1002/ejoc.202201180 |
op_rights |
© 2022 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
op_doi |
https://doi.org/10.1002/ejoc.202201180 |
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European Journal of Organic Chemistry |
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26 |
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2 |
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1768385632250363904 |