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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...

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Autores principales: Lux, Marcel, Klussmann, Martin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
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.
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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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