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Additions of Aldehyde-Derived Radicals and Nucleophilic N-Alkylindoles to Styrenes by Photoredox Catalysis
[Image: see text] The consecutive addition of acyl radicals and N-alkylindole nucleophiles to styrenes was established, as well as some additional radical–nucleophile combinations. Both aryl and aliphatic aldehydes give reasonable yields. The reaction proceeds best for α-substituted styrenes, effect...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American
Chemical Society
2020
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7304929/ https://www.ncbi.nlm.nih.gov/pubmed/32286834 http://dx.doi.org/10.1021/acs.orglett.0c01182 |
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author | Lux, Marcel Klussmann, Martin |
author_facet | Lux, Marcel Klussmann, Martin |
author_sort | Lux, Marcel |
collection | PubMed |
description | [Image: see text] The consecutive addition of acyl radicals and N-alkylindole nucleophiles to styrenes was established, as well as some additional radical–nucleophile combinations. Both aryl and aliphatic aldehydes give reasonable yields. The reaction proceeds best for α-substituted styrenes, effectively creating a quaternary all-carbon center. Some iridium-based photoredox systems are catalytically active; furthermore, a base is needed in this transformation. Radicals are formed by reductive perester cleavage and hydrogen atom transfer. |
format | Online Article Text |
id | pubmed-7304929 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American
Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-73049292020-06-22 Additions of Aldehyde-Derived Radicals and Nucleophilic N-Alkylindoles to Styrenes by Photoredox Catalysis Lux, Marcel Klussmann, Martin Org Lett [Image: see text] The consecutive addition of acyl radicals and N-alkylindole nucleophiles to styrenes was established, as well as some additional radical–nucleophile combinations. Both aryl and aliphatic aldehydes give reasonable yields. The reaction proceeds best for α-substituted styrenes, effectively creating a quaternary all-carbon center. Some iridium-based photoredox systems are catalytically active; furthermore, a base is needed in this transformation. Radicals are formed by reductive perester cleavage and hydrogen atom transfer. American Chemical Society 2020-04-14 2020-05-01 /pmc/articles/PMC7304929/ /pubmed/32286834 http://dx.doi.org/10.1021/acs.orglett.0c01182 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited. |
spellingShingle | Lux, Marcel Klussmann, Martin Additions of Aldehyde-Derived Radicals and Nucleophilic N-Alkylindoles to Styrenes by Photoredox Catalysis |
title | Additions of Aldehyde-Derived Radicals and Nucleophilic N-Alkylindoles to Styrenes by Photoredox Catalysis |
title_full | Additions of Aldehyde-Derived Radicals and Nucleophilic N-Alkylindoles to Styrenes by Photoredox Catalysis |
title_fullStr | Additions of Aldehyde-Derived Radicals and Nucleophilic N-Alkylindoles to Styrenes by Photoredox Catalysis |
title_full_unstemmed | Additions of Aldehyde-Derived Radicals and Nucleophilic N-Alkylindoles to Styrenes by Photoredox Catalysis |
title_short | Additions of Aldehyde-Derived Radicals and Nucleophilic N-Alkylindoles to Styrenes by Photoredox Catalysis |
title_sort | additions of aldehyde-derived radicals and nucleophilic n-alkylindoles to styrenes by photoredox catalysis |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7304929/ https://www.ncbi.nlm.nih.gov/pubmed/32286834 http://dx.doi.org/10.1021/acs.orglett.0c01182 |
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