Photoredox-Catalyzed Ketyl–Olefin Coupling for the Synthesis of Substituted Chromanols

[Image: see text] A visible light photoredox-catalyzed aldehyde olefin cyclization is reported. The method represents a formal hydroacylation of alkenes and alkynes and provides chromanol derivatives in good yields. The protocol takes advantage of the double role played by trialkylamines (NR(3)) whi...

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Autores principales: Fava, Eleonora, Nakajima, Masaki, Nguyen, Anh L. P., Rueping, Magnus
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5029965/
https://www.ncbi.nlm.nih.gov/pubmed/27442851
http://dx.doi.org/10.1021/acs.joc.6b01006
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author Fava, Eleonora
Nakajima, Masaki
Nguyen, Anh L. P.
Rueping, Magnus
author_facet Fava, Eleonora
Nakajima, Masaki
Nguyen, Anh L. P.
Rueping, Magnus
author_sort Fava, Eleonora
collection PubMed
description [Image: see text] A visible light photoredox-catalyzed aldehyde olefin cyclization is reported. The method represents a formal hydroacylation of alkenes and alkynes and provides chromanol derivatives in good yields. The protocol takes advantage of the double role played by trialkylamines (NR(3)) which act as (i) electron donors for reducing the catalyst and (ii) proton donors to activate the substrate via a proton-coupled electron transfer.
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spelling pubmed-50299652016-09-22 Photoredox-Catalyzed Ketyl–Olefin Coupling for the Synthesis of Substituted Chromanols Fava, Eleonora Nakajima, Masaki Nguyen, Anh L. P. Rueping, Magnus J Org Chem [Image: see text] A visible light photoredox-catalyzed aldehyde olefin cyclization is reported. The method represents a formal hydroacylation of alkenes and alkynes and provides chromanol derivatives in good yields. The protocol takes advantage of the double role played by trialkylamines (NR(3)) which act as (i) electron donors for reducing the catalyst and (ii) proton donors to activate the substrate via a proton-coupled electron transfer. American Chemical Society 2016-07-21 2016-08-19 /pmc/articles/PMC5029965/ /pubmed/27442851 http://dx.doi.org/10.1021/acs.joc.6b01006 Text en Copyright © 2016 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Fava, Eleonora
Nakajima, Masaki
Nguyen, Anh L. P.
Rueping, Magnus
Photoredox-Catalyzed Ketyl–Olefin Coupling for the Synthesis of Substituted Chromanols
title Photoredox-Catalyzed Ketyl–Olefin Coupling for the Synthesis of Substituted Chromanols
title_full Photoredox-Catalyzed Ketyl–Olefin Coupling for the Synthesis of Substituted Chromanols
title_fullStr Photoredox-Catalyzed Ketyl–Olefin Coupling for the Synthesis of Substituted Chromanols
title_full_unstemmed Photoredox-Catalyzed Ketyl–Olefin Coupling for the Synthesis of Substituted Chromanols
title_short Photoredox-Catalyzed Ketyl–Olefin Coupling for the Synthesis of Substituted Chromanols
title_sort photoredox-catalyzed ketyl–olefin coupling for the synthesis of substituted chromanols
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5029965/
https://www.ncbi.nlm.nih.gov/pubmed/27442851
http://dx.doi.org/10.1021/acs.joc.6b01006
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AT nguyenanhlp photoredoxcatalyzedketylolefincouplingforthesynthesisofsubstitutedchromanols
AT ruepingmagnus photoredoxcatalyzedketylolefincouplingforthesynthesisofsubstitutedchromanols

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