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Photosensitized Intermolecular Carboimination of Alkenes through the Persistent Radical Effect

An intermolecular, two‐component vicinal carboimination of alkenes has been accomplished by energy transfer catalysis. Oxime esters of alkyl carboxylic acids were used as bifunctional reagents to generate both alkyl and iminyl radicals. Subsequently, addition of the alkyl radical to an alkene genera...

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Autores principales: Patra, Tuhin, Bellotti, Peter, Strieth‐Kalthoff, Felix, Glorius, Frank
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7028066/
https://www.ncbi.nlm.nih.gov/pubmed/31794633
http://dx.doi.org/10.1002/anie.201912907
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author Patra, Tuhin
Bellotti, Peter
Strieth‐Kalthoff, Felix
Glorius, Frank
author_facet Patra, Tuhin
Bellotti, Peter
Strieth‐Kalthoff, Felix
Glorius, Frank
author_sort Patra, Tuhin
collection PubMed
description An intermolecular, two‐component vicinal carboimination of alkenes has been accomplished by energy transfer catalysis. Oxime esters of alkyl carboxylic acids were used as bifunctional reagents to generate both alkyl and iminyl radicals. Subsequently, addition of the alkyl radical to an alkene generates a transient radical for selective radical–radical cross‐coupling with the persistent iminyl radical. Furthermore, this process provides direct access to aliphatic primary amines and α‐amino acids by simple hydrolysis.
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spelling pubmed-70280662020-02-25 Photosensitized Intermolecular Carboimination of Alkenes through the Persistent Radical Effect Patra, Tuhin Bellotti, Peter Strieth‐Kalthoff, Felix Glorius, Frank Angew Chem Int Ed Engl Communications An intermolecular, two‐component vicinal carboimination of alkenes has been accomplished by energy transfer catalysis. Oxime esters of alkyl carboxylic acids were used as bifunctional reagents to generate both alkyl and iminyl radicals. Subsequently, addition of the alkyl radical to an alkene generates a transient radical for selective radical–radical cross‐coupling with the persistent iminyl radical. Furthermore, this process provides direct access to aliphatic primary amines and α‐amino acids by simple hydrolysis. John Wiley and Sons Inc. 2020-01-21 2020-02-17 /pmc/articles/PMC7028066/ /pubmed/31794633 http://dx.doi.org/10.1002/anie.201912907 Text en © 2019 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/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
Patra, Tuhin
Bellotti, Peter
Strieth‐Kalthoff, Felix
Glorius, Frank
Photosensitized Intermolecular Carboimination of Alkenes through the Persistent Radical Effect
title Photosensitized Intermolecular Carboimination of Alkenes through the Persistent Radical Effect
title_full Photosensitized Intermolecular Carboimination of Alkenes through the Persistent Radical Effect
title_fullStr Photosensitized Intermolecular Carboimination of Alkenes through the Persistent Radical Effect
title_full_unstemmed Photosensitized Intermolecular Carboimination of Alkenes through the Persistent Radical Effect
title_short Photosensitized Intermolecular Carboimination of Alkenes through the Persistent Radical Effect
title_sort photosensitized intermolecular carboimination of alkenes through the persistent radical effect
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7028066/
https://www.ncbi.nlm.nih.gov/pubmed/31794633
http://dx.doi.org/10.1002/anie.201912907
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