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Photocatalytic synthesis of tetra-substituted furans promoted by carbon dioxide

We report a simple protocol for the transition metal-free, visible-light-driven conversion of 1,3-diketones to tetra-substituted furan skeleton compounds in carbon dioxide (CO(2)) atmosphere under mild conditions. It was found that CO(2) could be incorporated at the diketone enolic OH position, whic...

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Detalles Bibliográficos
Autores principales: Tian, Ya-Ming, Wang, Huaiju, Ritu, König, Burkhard
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8694347/
https://www.ncbi.nlm.nih.gov/pubmed/35059173
http://dx.doi.org/10.1039/d1sc06403g
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author Tian, Ya-Ming
Wang, Huaiju
Ritu,
König, Burkhard
author_facet Tian, Ya-Ming
Wang, Huaiju
Ritu,
König, Burkhard
author_sort Tian, Ya-Ming
collection PubMed
description We report a simple protocol for the transition metal-free, visible-light-driven conversion of 1,3-diketones to tetra-substituted furan skeleton compounds in carbon dioxide (CO(2)) atmosphere under mild conditions. It was found that CO(2) could be incorporated at the diketone enolic OH position, which was key to enabling the cleavage of a C–O bond during the rearrangement of a cyclopropane intermediate. This method allows for the same-pot construction of two isomers of the high-value tetra-substituted furan scaffold. The synthetic scope and preliminary mechanistic investigations are presented.
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spelling pubmed-86943472022-01-19 Photocatalytic synthesis of tetra-substituted furans promoted by carbon dioxide Tian, Ya-Ming Wang, Huaiju Ritu, König, Burkhard Chem Sci Chemistry We report a simple protocol for the transition metal-free, visible-light-driven conversion of 1,3-diketones to tetra-substituted furan skeleton compounds in carbon dioxide (CO(2)) atmosphere under mild conditions. It was found that CO(2) could be incorporated at the diketone enolic OH position, which was key to enabling the cleavage of a C–O bond during the rearrangement of a cyclopropane intermediate. This method allows for the same-pot construction of two isomers of the high-value tetra-substituted furan scaffold. The synthetic scope and preliminary mechanistic investigations are presented. The Royal Society of Chemistry 2021-12-06 /pmc/articles/PMC8694347/ /pubmed/35059173 http://dx.doi.org/10.1039/d1sc06403g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Tian, Ya-Ming
Wang, Huaiju
Ritu,
König, Burkhard
Photocatalytic synthesis of tetra-substituted furans promoted by carbon dioxide
title Photocatalytic synthesis of tetra-substituted furans promoted by carbon dioxide
title_full Photocatalytic synthesis of tetra-substituted furans promoted by carbon dioxide
title_fullStr Photocatalytic synthesis of tetra-substituted furans promoted by carbon dioxide
title_full_unstemmed Photocatalytic synthesis of tetra-substituted furans promoted by carbon dioxide
title_short Photocatalytic synthesis of tetra-substituted furans promoted by carbon dioxide
title_sort photocatalytic synthesis of tetra-substituted furans promoted by carbon dioxide
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8694347/
https://www.ncbi.nlm.nih.gov/pubmed/35059173
http://dx.doi.org/10.1039/d1sc06403g
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AT ritu photocatalyticsynthesisoftetrasubstitutedfuranspromotedbycarbondioxide
AT konigburkhard photocatalyticsynthesisoftetrasubstitutedfuranspromotedbycarbondioxide