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Photoinduced site-selective alkenylation of alkanes and aldehydes with aryl alkenes
The dehydrogenative alkenylation of C-H bonds with alkenes represents an atom- and step-economical approach for olefin synthesis and molecular editing. Site-selective alkenylation of alkanes and aldehydes with the C-H substrate as the limiting reagent holds significant synthetic value. We herein rep...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7181776/ https://www.ncbi.nlm.nih.gov/pubmed/32327665 http://dx.doi.org/10.1038/s41467-020-15878-6 |
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author | Cao, Hui Kuang, Yulong Shi, Xiangcheng Wong, Koi Lin Tan, Boon Beng Kwan, Jeric Mun Chung Liu, Xiaogang Wu, Jie |
author_facet | Cao, Hui Kuang, Yulong Shi, Xiangcheng Wong, Koi Lin Tan, Boon Beng Kwan, Jeric Mun Chung Liu, Xiaogang Wu, Jie |
author_sort | Cao, Hui |
collection | PubMed |
description | The dehydrogenative alkenylation of C-H bonds with alkenes represents an atom- and step-economical approach for olefin synthesis and molecular editing. Site-selective alkenylation of alkanes and aldehydes with the C-H substrate as the limiting reagent holds significant synthetic value. We herein report a photocatalytic method for the direct alkenylation of alkanes and aldehydes with aryl alkenes in the absence of any external oxidant. A diverse range of commodity feedstocks and pharmaceutical compounds are smoothly alkenylated in useful yields with the C-H partner as the limiting reagent. The late-stage alkenylation of complex molecules occurs with high levels of site selectivity for sterically accessible and electron-rich C-H bonds. This strategy relies on the synergistic combination of direct hydrogen atom transfer photocatalysis with cobaloxime-mediated hydrogen-evolution cross-coupling, which promises to inspire additional perspectives for selective C-H functionalizations in a green manner. |
format | Online Article Text |
id | pubmed-7181776 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-71817762020-04-29 Photoinduced site-selective alkenylation of alkanes and aldehydes with aryl alkenes Cao, Hui Kuang, Yulong Shi, Xiangcheng Wong, Koi Lin Tan, Boon Beng Kwan, Jeric Mun Chung Liu, Xiaogang Wu, Jie Nat Commun Article The dehydrogenative alkenylation of C-H bonds with alkenes represents an atom- and step-economical approach for olefin synthesis and molecular editing. Site-selective alkenylation of alkanes and aldehydes with the C-H substrate as the limiting reagent holds significant synthetic value. We herein report a photocatalytic method for the direct alkenylation of alkanes and aldehydes with aryl alkenes in the absence of any external oxidant. A diverse range of commodity feedstocks and pharmaceutical compounds are smoothly alkenylated in useful yields with the C-H partner as the limiting reagent. The late-stage alkenylation of complex molecules occurs with high levels of site selectivity for sterically accessible and electron-rich C-H bonds. This strategy relies on the synergistic combination of direct hydrogen atom transfer photocatalysis with cobaloxime-mediated hydrogen-evolution cross-coupling, which promises to inspire additional perspectives for selective C-H functionalizations in a green manner. Nature Publishing Group UK 2020-04-23 /pmc/articles/PMC7181776/ /pubmed/32327665 http://dx.doi.org/10.1038/s41467-020-15878-6 Text en © The Author(s) 2020 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/. |
spellingShingle | Article Cao, Hui Kuang, Yulong Shi, Xiangcheng Wong, Koi Lin Tan, Boon Beng Kwan, Jeric Mun Chung Liu, Xiaogang Wu, Jie Photoinduced site-selective alkenylation of alkanes and aldehydes with aryl alkenes |
title | Photoinduced site-selective alkenylation of alkanes and aldehydes with aryl alkenes |
title_full | Photoinduced site-selective alkenylation of alkanes and aldehydes with aryl alkenes |
title_fullStr | Photoinduced site-selective alkenylation of alkanes and aldehydes with aryl alkenes |
title_full_unstemmed | Photoinduced site-selective alkenylation of alkanes and aldehydes with aryl alkenes |
title_short | Photoinduced site-selective alkenylation of alkanes and aldehydes with aryl alkenes |
title_sort | photoinduced site-selective alkenylation of alkanes and aldehydes with aryl alkenes |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7181776/ https://www.ncbi.nlm.nih.gov/pubmed/32327665 http://dx.doi.org/10.1038/s41467-020-15878-6 |
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