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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...

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Autores principales: Cao, Hui, Kuang, Yulong, Shi, Xiangcheng, Wong, Koi Lin, Tan, Boon Beng, Kwan, Jeric Mun Chung, Liu, Xiaogang, Wu, Jie
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2020
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.
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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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