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Photoinitiated Three-Component α-Perfluoroalkyl-β-heteroarylation of Unactivated Alkenes via Electron Catalysis
[Image: see text] A visible-light-initiated α-perfluoroalkyl-β-heteroarylation of various alkenes with perfluoroalkyl iodides and quinoxalin-2(1H)-ones is presented. This three-component radical cascade reaction allows an efficient synthesis of a range of perfluoroalkyl containing quinoxalin-2(1H)-o...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2018
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6326532/ https://www.ncbi.nlm.nih.gov/pubmed/30576162 http://dx.doi.org/10.1021/acs.orglett.8b03849 |
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author | Zheng, Danqing Studer, Armido |
author_facet | Zheng, Danqing Studer, Armido |
author_sort | Zheng, Danqing |
collection | PubMed |
description | [Image: see text] A visible-light-initiated α-perfluoroalkyl-β-heteroarylation of various alkenes with perfluoroalkyl iodides and quinoxalin-2(1H)-ones is presented. This three-component radical cascade reaction allows an efficient synthesis of a range of perfluoroalkyl containing quinoxalin-2(1H)-one derivatives in moderate to excellent yields under mild conditions. Reactions proceed via acidic aminyl radicals that are readily deprotonated to give the corresponding radical anions able to sustain the radical chain as single electron transfer reducing reagents. Hence, the overall cascade classifies as an electron-catalyzed process. |
format | Online Article Text |
id | pubmed-6326532 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-63265322019-01-17 Photoinitiated Three-Component α-Perfluoroalkyl-β-heteroarylation of Unactivated Alkenes via Electron Catalysis Zheng, Danqing Studer, Armido Org Lett [Image: see text] A visible-light-initiated α-perfluoroalkyl-β-heteroarylation of various alkenes with perfluoroalkyl iodides and quinoxalin-2(1H)-ones is presented. This three-component radical cascade reaction allows an efficient synthesis of a range of perfluoroalkyl containing quinoxalin-2(1H)-one derivatives in moderate to excellent yields under mild conditions. Reactions proceed via acidic aminyl radicals that are readily deprotonated to give the corresponding radical anions able to sustain the radical chain as single electron transfer reducing reagents. Hence, the overall cascade classifies as an electron-catalyzed process. American Chemical Society 2018-12-21 2019-01-04 /pmc/articles/PMC6326532/ /pubmed/30576162 http://dx.doi.org/10.1021/acs.orglett.8b03849 Text en Copyright © 2018 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | Zheng, Danqing Studer, Armido Photoinitiated Three-Component α-Perfluoroalkyl-β-heteroarylation of Unactivated Alkenes via Electron Catalysis |
title | Photoinitiated Three-Component α-Perfluoroalkyl-β-heteroarylation of Unactivated Alkenes via Electron Catalysis |
title_full | Photoinitiated Three-Component α-Perfluoroalkyl-β-heteroarylation of Unactivated Alkenes via Electron Catalysis |
title_fullStr | Photoinitiated Three-Component α-Perfluoroalkyl-β-heteroarylation of Unactivated Alkenes via Electron Catalysis |
title_full_unstemmed | Photoinitiated Three-Component α-Perfluoroalkyl-β-heteroarylation of Unactivated Alkenes via Electron Catalysis |
title_short | Photoinitiated Three-Component α-Perfluoroalkyl-β-heteroarylation of Unactivated Alkenes via Electron Catalysis |
title_sort | photoinitiated three-component α-perfluoroalkyl-β-heteroarylation of unactivated alkenes via electron catalysis |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6326532/ https://www.ncbi.nlm.nih.gov/pubmed/30576162 http://dx.doi.org/10.1021/acs.orglett.8b03849 |
work_keys_str_mv | AT zhengdanqing photoinitiatedthreecomponentaperfluoroalkylbheteroarylationofunactivatedalkenesviaelectroncatalysis AT studerarmido photoinitiatedthreecomponentaperfluoroalkylbheteroarylationofunactivatedalkenesviaelectroncatalysis |