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Metal-free alcohol-directed regioselective heteroarylation of remote unactivated C(sp(3))–H bonds
Construction of C–C bonds via alkoxy radical-mediated remote C(sp(3))–H functionalization is largely unexplored, as it is a formidable challenge to directly generate alkoxy radicals from alcohols due to the high bond dissociation energy (BDE) of O–H bonds. Disclosed herein is a practical and elusive...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6104081/ https://www.ncbi.nlm.nih.gov/pubmed/30131495 http://dx.doi.org/10.1038/s41467-018-05522-9 |
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author | Wu, Xinxin Zhang, Hong Tang, Nana Wu, Zhen Wang, Dongping Ji, Meishan Xu, Yan Wang, Min Zhu, Chen |
author_facet | Wu, Xinxin Zhang, Hong Tang, Nana Wu, Zhen Wang, Dongping Ji, Meishan Xu, Yan Wang, Min Zhu, Chen |
author_sort | Wu, Xinxin |
collection | PubMed |
description | Construction of C–C bonds via alkoxy radical-mediated remote C(sp(3))–H functionalization is largely unexplored, as it is a formidable challenge to directly generate alkoxy radicals from alcohols due to the high bond dissociation energy (BDE) of O–H bonds. Disclosed herein is a practical and elusive metal-free alcohol-directed heteroarylation of remote unactivated C(sp(3))–H bonds. Phenyliodine bis(trifluoroacetate) (PIFA) is used as the only reagent to enable the coupling of alcohols and heteroaryls. Alkoxy radicals are readily generated from free alcohols under the irradiation of visible light, which trigger the regioselective hydrogen-atom transfer (HAT). A wide range of functional groups are compatible with the mild reaction conditions. Two unactivated C–H bonds are cleaved and one new C–C bond is constructed during the reaction. This protocol provides an efficient strategy for the late-stage functionalization of alcohols and heteroaryls. |
format | Online Article Text |
id | pubmed-6104081 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-61040812018-08-23 Metal-free alcohol-directed regioselective heteroarylation of remote unactivated C(sp(3))–H bonds Wu, Xinxin Zhang, Hong Tang, Nana Wu, Zhen Wang, Dongping Ji, Meishan Xu, Yan Wang, Min Zhu, Chen Nat Commun Article Construction of C–C bonds via alkoxy radical-mediated remote C(sp(3))–H functionalization is largely unexplored, as it is a formidable challenge to directly generate alkoxy radicals from alcohols due to the high bond dissociation energy (BDE) of O–H bonds. Disclosed herein is a practical and elusive metal-free alcohol-directed heteroarylation of remote unactivated C(sp(3))–H bonds. Phenyliodine bis(trifluoroacetate) (PIFA) is used as the only reagent to enable the coupling of alcohols and heteroaryls. Alkoxy radicals are readily generated from free alcohols under the irradiation of visible light, which trigger the regioselective hydrogen-atom transfer (HAT). A wide range of functional groups are compatible with the mild reaction conditions. Two unactivated C–H bonds are cleaved and one new C–C bond is constructed during the reaction. This protocol provides an efficient strategy for the late-stage functionalization of alcohols and heteroaryls. Nature Publishing Group UK 2018-08-21 /pmc/articles/PMC6104081/ /pubmed/30131495 http://dx.doi.org/10.1038/s41467-018-05522-9 Text en © The Author(s) 2018 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 Wu, Xinxin Zhang, Hong Tang, Nana Wu, Zhen Wang, Dongping Ji, Meishan Xu, Yan Wang, Min Zhu, Chen Metal-free alcohol-directed regioselective heteroarylation of remote unactivated C(sp(3))–H bonds |
title | Metal-free alcohol-directed regioselective heteroarylation of remote unactivated C(sp(3))–H bonds |
title_full | Metal-free alcohol-directed regioselective heteroarylation of remote unactivated C(sp(3))–H bonds |
title_fullStr | Metal-free alcohol-directed regioselective heteroarylation of remote unactivated C(sp(3))–H bonds |
title_full_unstemmed | Metal-free alcohol-directed regioselective heteroarylation of remote unactivated C(sp(3))–H bonds |
title_short | Metal-free alcohol-directed regioselective heteroarylation of remote unactivated C(sp(3))–H bonds |
title_sort | metal-free alcohol-directed regioselective heteroarylation of remote unactivated c(sp(3))–h bonds |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6104081/ https://www.ncbi.nlm.nih.gov/pubmed/30131495 http://dx.doi.org/10.1038/s41467-018-05522-9 |
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