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Diverse reactivity of the gem-difluorovinyl iodonium salt for direct incorporation of the difluoroethylene group into N- and O-nucleophiles
The synthesis of gem-difluoroethylene compounds remains a difficult task in organic synthesis. Here, the direct difluoroethylation reactions of N- and O-nucleophiles including amides and acids were realized with a hypervalent iodine reagent: gem-difluorovinyl iodonium salt (DFVI). The reactions were...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9814539/ https://www.ncbi.nlm.nih.gov/pubmed/36697903 http://dx.doi.org/10.1038/s42004-022-00772-7 |
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author | Ge, Chenxin Wang, Bin Jiang, Yunchen Chen, Chao |
author_facet | Ge, Chenxin Wang, Bin Jiang, Yunchen Chen, Chao |
author_sort | Ge, Chenxin |
collection | PubMed |
description | The synthesis of gem-difluoroethylene compounds remains a difficult task in organic synthesis. Here, the direct difluoroethylation reactions of N- and O-nucleophiles including amides and acids were realized with a hypervalent iodine reagent: gem-difluorovinyl iodonium salt (DFVI). The reactions were accomplished via a neighbouring group rearrangement. The gem-difluorovinyl iodonium salt was found to display diverse reactivity due to its unique electronic effect and was applied to the incorporation of difluoroethylene group, including difluorovinylation of carboxylic acids, difluorovinylation and 1,3-cyclic fluorovinylation of amides and 1,1-cyclic difluoroethylation of amines. |
format | Online Article Text |
id | pubmed-9814539 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-98145392023-01-10 Diverse reactivity of the gem-difluorovinyl iodonium salt for direct incorporation of the difluoroethylene group into N- and O-nucleophiles Ge, Chenxin Wang, Bin Jiang, Yunchen Chen, Chao Commun Chem Article The synthesis of gem-difluoroethylene compounds remains a difficult task in organic synthesis. Here, the direct difluoroethylation reactions of N- and O-nucleophiles including amides and acids were realized with a hypervalent iodine reagent: gem-difluorovinyl iodonium salt (DFVI). The reactions were accomplished via a neighbouring group rearrangement. The gem-difluorovinyl iodonium salt was found to display diverse reactivity due to its unique electronic effect and was applied to the incorporation of difluoroethylene group, including difluorovinylation of carboxylic acids, difluorovinylation and 1,3-cyclic fluorovinylation of amides and 1,1-cyclic difluoroethylation of amines. Nature Publishing Group UK 2022-12-03 /pmc/articles/PMC9814539/ /pubmed/36697903 http://dx.doi.org/10.1038/s42004-022-00772-7 Text en © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/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/ (https://creativecommons.org/licenses/by/4.0/) . |
spellingShingle | Article Ge, Chenxin Wang, Bin Jiang, Yunchen Chen, Chao Diverse reactivity of the gem-difluorovinyl iodonium salt for direct incorporation of the difluoroethylene group into N- and O-nucleophiles |
title | Diverse reactivity of the gem-difluorovinyl iodonium salt for direct incorporation of the difluoroethylene group into N- and O-nucleophiles |
title_full | Diverse reactivity of the gem-difluorovinyl iodonium salt for direct incorporation of the difluoroethylene group into N- and O-nucleophiles |
title_fullStr | Diverse reactivity of the gem-difluorovinyl iodonium salt for direct incorporation of the difluoroethylene group into N- and O-nucleophiles |
title_full_unstemmed | Diverse reactivity of the gem-difluorovinyl iodonium salt for direct incorporation of the difluoroethylene group into N- and O-nucleophiles |
title_short | Diverse reactivity of the gem-difluorovinyl iodonium salt for direct incorporation of the difluoroethylene group into N- and O-nucleophiles |
title_sort | diverse reactivity of the gem-difluorovinyl iodonium salt for direct incorporation of the difluoroethylene group into n- and o-nucleophiles |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9814539/ https://www.ncbi.nlm.nih.gov/pubmed/36697903 http://dx.doi.org/10.1038/s42004-022-00772-7 |
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