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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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10108053/ https://www.ncbi.nlm.nih.gov/pubmed/37082528 http://dx.doi.org/10.1002/ejoc.202201180 |
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author | Müller, Kilian A. Nagel, Carolin H. Breder, Alexander |
author_facet | Müller, Kilian A. Nagel, Carolin H. Breder, Alexander |
author_sort | Müller, Kilian A. |
collection | PubMed |
description | 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 | Online Article Text |
id | pubmed-10108053 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-101080532023-04-18 Synthesis of 1,3‐Dioxan‐2‐ones by Photo‐Aerobic Selenium‐π‐Acid Multicatalysis Müller, Kilian A. Nagel, Carolin H. Breder, Alexander European J Org Chem Research Articles 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. John Wiley and Sons Inc. 2022-12-22 2023-01-10 /pmc/articles/PMC10108053/ /pubmed/37082528 http://dx.doi.org/10.1002/ejoc.202201180 Text en © 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. |
spellingShingle | Research Articles Müller, Kilian A. Nagel, Carolin H. Breder, Alexander Synthesis of 1,3‐Dioxan‐2‐ones by Photo‐Aerobic Selenium‐π‐Acid Multicatalysis |
title | 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_short | 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 |
topic | Research Articles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10108053/ https://www.ncbi.nlm.nih.gov/pubmed/37082528 http://dx.doi.org/10.1002/ejoc.202201180 |
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