Reductive Umpolung of Carbonyl Derivatives with Visible‐Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α‐Amino Radicals and Ketyl Radicals

Visible‐light‐mediated photoredox‐catalyzed aldimine–aniline and aldehyde–aniline couplings have been realized. The reductive single electron transfer (SET) umpolung of various carbonyl derivatives enabled the generation of intermediary ketyl and α‐amino radical anions, which were utilized for the s...

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Autores principales: Fava, Eleonora, Millet, Anthony, Nakajima, Masaki, Loescher, Sebastian, Rueping, Magnus
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5021176/
https://www.ncbi.nlm.nih.gov/pubmed/27136443
http://dx.doi.org/10.1002/anie.201511235
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author Fava, Eleonora
Millet, Anthony
Nakajima, Masaki
Loescher, Sebastian
Rueping, Magnus
author_facet Fava, Eleonora
Millet, Anthony
Nakajima, Masaki
Loescher, Sebastian
Rueping, Magnus
author_sort Fava, Eleonora
collection PubMed
description Visible‐light‐mediated photoredox‐catalyzed aldimine–aniline and aldehyde–aniline couplings have been realized. The reductive single electron transfer (SET) umpolung of various carbonyl derivatives enabled the generation of intermediary ketyl and α‐amino radical anions, which were utilized for the synthesis of unsymmetrically substituted 1,2‐diamines and amino alcohols.
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spelling pubmed-50211762016-09-23 Reductive Umpolung of Carbonyl Derivatives with Visible‐Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α‐Amino Radicals and Ketyl Radicals Fava, Eleonora Millet, Anthony Nakajima, Masaki Loescher, Sebastian Rueping, Magnus Angew Chem Int Ed Engl Communications Visible‐light‐mediated photoredox‐catalyzed aldimine–aniline and aldehyde–aniline couplings have been realized. The reductive single electron transfer (SET) umpolung of various carbonyl derivatives enabled the generation of intermediary ketyl and α‐amino radical anions, which were utilized for the synthesis of unsymmetrically substituted 1,2‐diamines and amino alcohols. John Wiley and Sons Inc. 2016-05-02 2016-06-01 /pmc/articles/PMC5021176/ /pubmed/27136443 http://dx.doi.org/10.1002/anie.201511235 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial (http://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Fava, Eleonora
Millet, Anthony
Nakajima, Masaki
Loescher, Sebastian
Rueping, Magnus
Reductive Umpolung of Carbonyl Derivatives with Visible‐Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α‐Amino Radicals and Ketyl Radicals
title Reductive Umpolung of Carbonyl Derivatives with Visible‐Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α‐Amino Radicals and Ketyl Radicals
title_full Reductive Umpolung of Carbonyl Derivatives with Visible‐Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α‐Amino Radicals and Ketyl Radicals
title_fullStr Reductive Umpolung of Carbonyl Derivatives with Visible‐Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α‐Amino Radicals and Ketyl Radicals
title_full_unstemmed Reductive Umpolung of Carbonyl Derivatives with Visible‐Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α‐Amino Radicals and Ketyl Radicals
title_short Reductive Umpolung of Carbonyl Derivatives with Visible‐Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α‐Amino Radicals and Ketyl Radicals
title_sort reductive umpolung of carbonyl derivatives with visible‐light photoredox catalysis: direct access to vicinal diamines and amino alcohols via α‐amino radicals and ketyl radicals
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5021176/
https://www.ncbi.nlm.nih.gov/pubmed/27136443
http://dx.doi.org/10.1002/anie.201511235
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