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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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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. |
format | Online Article Text |
id | pubmed-8694347 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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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