Cargando…

Integrated redox-active reagents for photoinduced regio- and stereoselective fluorocarboborylation

Vinylboronates and alkylboronates are key components in variegated transformations in all facets of chemical science. The synthesis of vinylboronates and alkylboronates suffers from step-tedious and poor stereoselective procedures. We have developed a regulated radical difunctionalization strategy f...

Descripción completa

Detalles Bibliográficos
Autores principales: Zhang, Weigang, Zou, Zhenlei, Zhao, Wenxuan, Lu, Shuo, Wu, Zhengguang, Huang, Mengjun, Wang, Xiaochen, Wang, Yi, Liang, Yong, Zhu, Yi, Zheng, Youxuan, Pan, Yi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7244735/
https://www.ncbi.nlm.nih.gov/pubmed/32444596
http://dx.doi.org/10.1038/s41467-020-16477-1
_version_ 1783537623123361792
author Zhang, Weigang
Zou, Zhenlei
Zhao, Wenxuan
Lu, Shuo
Wu, Zhengguang
Huang, Mengjun
Wang, Xiaochen
Wang, Yi
Liang, Yong
Zhu, Yi
Zheng, Youxuan
Pan, Yi
author_facet Zhang, Weigang
Zou, Zhenlei
Zhao, Wenxuan
Lu, Shuo
Wu, Zhengguang
Huang, Mengjun
Wang, Xiaochen
Wang, Yi
Liang, Yong
Zhu, Yi
Zheng, Youxuan
Pan, Yi
author_sort Zhang, Weigang
collection PubMed
description Vinylboronates and alkylboronates are key components in variegated transformations in all facets of chemical science. The synthesis of vinylboronates and alkylboronates suffers from step-tedious and poor stereoselective procedures. We have developed a regulated radical difunctionalization strategy for the construction of fluorine-containing vinylboronates and alkylboronates with an integrated redox-active reagent IMDN-SO(2)R(F). This bench-stable imidazolium sulfonate cationic salt offers a scalable and operational protocol for the fluoroalkylation-borylation of unsaturated hydrocarbons in a high regio- and stereoselective manner. The products can be further transformed into valuable fluorinated building blocks.
format Online
Article
Text
id pubmed-7244735
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher Nature Publishing Group UK
record_format MEDLINE/PubMed
spelling pubmed-72447352020-06-03 Integrated redox-active reagents for photoinduced regio- and stereoselective fluorocarboborylation Zhang, Weigang Zou, Zhenlei Zhao, Wenxuan Lu, Shuo Wu, Zhengguang Huang, Mengjun Wang, Xiaochen Wang, Yi Liang, Yong Zhu, Yi Zheng, Youxuan Pan, Yi Nat Commun Article Vinylboronates and alkylboronates are key components in variegated transformations in all facets of chemical science. The synthesis of vinylboronates and alkylboronates suffers from step-tedious and poor stereoselective procedures. We have developed a regulated radical difunctionalization strategy for the construction of fluorine-containing vinylboronates and alkylboronates with an integrated redox-active reagent IMDN-SO(2)R(F). This bench-stable imidazolium sulfonate cationic salt offers a scalable and operational protocol for the fluoroalkylation-borylation of unsaturated hydrocarbons in a high regio- and stereoselective manner. The products can be further transformed into valuable fluorinated building blocks. Nature Publishing Group UK 2020-05-22 /pmc/articles/PMC7244735/ /pubmed/32444596 http://dx.doi.org/10.1038/s41467-020-16477-1 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
Zhang, Weigang
Zou, Zhenlei
Zhao, Wenxuan
Lu, Shuo
Wu, Zhengguang
Huang, Mengjun
Wang, Xiaochen
Wang, Yi
Liang, Yong
Zhu, Yi
Zheng, Youxuan
Pan, Yi
Integrated redox-active reagents for photoinduced regio- and stereoselective fluorocarboborylation
title Integrated redox-active reagents for photoinduced regio- and stereoselective fluorocarboborylation
title_full Integrated redox-active reagents for photoinduced regio- and stereoselective fluorocarboborylation
title_fullStr Integrated redox-active reagents for photoinduced regio- and stereoselective fluorocarboborylation
title_full_unstemmed Integrated redox-active reagents for photoinduced regio- and stereoselective fluorocarboborylation
title_short Integrated redox-active reagents for photoinduced regio- and stereoselective fluorocarboborylation
title_sort integrated redox-active reagents for photoinduced regio- and stereoselective fluorocarboborylation
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7244735/
https://www.ncbi.nlm.nih.gov/pubmed/32444596
http://dx.doi.org/10.1038/s41467-020-16477-1
work_keys_str_mv AT zhangweigang integratedredoxactivereagentsforphotoinducedregioandstereoselectivefluorocarboborylation
AT zouzhenlei integratedredoxactivereagentsforphotoinducedregioandstereoselectivefluorocarboborylation
AT zhaowenxuan integratedredoxactivereagentsforphotoinducedregioandstereoselectivefluorocarboborylation
AT lushuo integratedredoxactivereagentsforphotoinducedregioandstereoselectivefluorocarboborylation
AT wuzhengguang integratedredoxactivereagentsforphotoinducedregioandstereoselectivefluorocarboborylation
AT huangmengjun integratedredoxactivereagentsforphotoinducedregioandstereoselectivefluorocarboborylation
AT wangxiaochen integratedredoxactivereagentsforphotoinducedregioandstereoselectivefluorocarboborylation
AT wangyi integratedredoxactivereagentsforphotoinducedregioandstereoselectivefluorocarboborylation
AT liangyong integratedredoxactivereagentsforphotoinducedregioandstereoselectivefluorocarboborylation
AT zhuyi integratedredoxactivereagentsforphotoinducedregioandstereoselectivefluorocarboborylation
AT zhengyouxuan integratedredoxactivereagentsforphotoinducedregioandstereoselectivefluorocarboborylation
AT panyi integratedredoxactivereagentsforphotoinducedregioandstereoselectivefluorocarboborylation