Photoredox‐Catalyzed Addition of Carbamoyl Radicals to Olefins: A 1,4‐Dihydropyridine Approach

Functionalization with C1‐building blocks are key synthetic methods in organic synthesis. The low reactivity of the most abundant C(1)‐molecule, carbon dioxide, makes alternative carboxylation reactions with CO(2)‐surrogates especially important. We report a photoredox‐catalyzed protocol for alkene...

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Autores principales: Cardinale, Luana, Konev, Mikhail O., Jacobi von Wangelin, Axel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7384035/
https://www.ncbi.nlm.nih.gov/pubmed/32428293
http://dx.doi.org/10.1002/chem.202002410
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author Cardinale, Luana
Konev, Mikhail O.
Jacobi von Wangelin, Axel
author_facet Cardinale, Luana
Konev, Mikhail O.
Jacobi von Wangelin, Axel
author_sort Cardinale, Luana
collection PubMed
description Functionalization with C1‐building blocks are key synthetic methods in organic synthesis. The low reactivity of the most abundant C(1)‐molecule, carbon dioxide, makes alternative carboxylation reactions with CO(2)‐surrogates especially important. We report a photoredox‐catalyzed protocol for alkene carbamoylations. Readily accessible 4‐carboxamido‐Hantzsch esters serve as convenient starting materials that generate carbamoyl radicals upon visible light‐mediated single‐electron transfer. Addition to various alkenes proceeded with high levels of regio‐ and chemoselectivity.
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spelling pubmed-73840352020-07-28 Photoredox‐Catalyzed Addition of Carbamoyl Radicals to Olefins: A 1,4‐Dihydropyridine Approach Cardinale, Luana Konev, Mikhail O. Jacobi von Wangelin, Axel Chemistry Communications Functionalization with C1‐building blocks are key synthetic methods in organic synthesis. The low reactivity of the most abundant C(1)‐molecule, carbon dioxide, makes alternative carboxylation reactions with CO(2)‐surrogates especially important. We report a photoredox‐catalyzed protocol for alkene carbamoylations. Readily accessible 4‐carboxamido‐Hantzsch esters serve as convenient starting materials that generate carbamoyl radicals upon visible light‐mediated single‐electron transfer. Addition to various alkenes proceeded with high levels of regio‐ and chemoselectivity. John Wiley and Sons Inc. 2020-06-11 2020-07-02 /pmc/articles/PMC7384035/ /pubmed/32428293 http://dx.doi.org/10.1002/chem.202002410 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Cardinale, Luana
Konev, Mikhail O.
Jacobi von Wangelin, Axel
Photoredox‐Catalyzed Addition of Carbamoyl Radicals to Olefins: A 1,4‐Dihydropyridine Approach
title Photoredox‐Catalyzed Addition of Carbamoyl Radicals to Olefins: A 1,4‐Dihydropyridine Approach
title_full Photoredox‐Catalyzed Addition of Carbamoyl Radicals to Olefins: A 1,4‐Dihydropyridine Approach
title_fullStr Photoredox‐Catalyzed Addition of Carbamoyl Radicals to Olefins: A 1,4‐Dihydropyridine Approach
title_full_unstemmed Photoredox‐Catalyzed Addition of Carbamoyl Radicals to Olefins: A 1,4‐Dihydropyridine Approach
title_short Photoredox‐Catalyzed Addition of Carbamoyl Radicals to Olefins: A 1,4‐Dihydropyridine Approach
title_sort photoredox‐catalyzed addition of carbamoyl radicals to olefins: a 1,4‐dihydropyridine approach
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7384035/
https://www.ncbi.nlm.nih.gov/pubmed/32428293
http://dx.doi.org/10.1002/chem.202002410
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AT jacobivonwangelinaxel photoredoxcatalyzedadditionofcarbamoylradicalstoolefinsa14dihydropyridineapproach

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