Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N–C Cleavage of Imides

[Image: see text] An electrophilic, imide-based, visible-light-promoted photoredox/Ni-catalyzed cross-coupling reaction for the synthesis of aliphatic ketones has been developed. This protocol proceeds through N–C(O) bond activation, made possible through the lower activation energy for metal insert...

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Autores principales: Amani, Javad, Alam, Rauful, Badir, Shorouk, Molander, Gary A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5423445/
https://www.ncbi.nlm.nih.gov/pubmed/28445061
http://dx.doi.org/10.1021/acs.orglett.7b00989
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author Amani, Javad
Alam, Rauful
Badir, Shorouk
Molander, Gary A.
author_facet Amani, Javad
Alam, Rauful
Badir, Shorouk
Molander, Gary A.
author_sort Amani, Javad
collection PubMed
description [Image: see text] An electrophilic, imide-based, visible-light-promoted photoredox/Ni-catalyzed cross-coupling reaction for the synthesis of aliphatic ketones has been developed. This protocol proceeds through N–C(O) bond activation, made possible through the lower activation energy for metal insertion into this bond due to delocalization of the lone pair of electrons on the nitrogen by electron-withdrawing groups. The operationally simple and mild cross-coupling reaction is performed at ambient temperature and exhibits tolerance for a variety of functional groups.
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spelling pubmed-54234452018-04-26 Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N–C Cleavage of Imides Amani, Javad Alam, Rauful Badir, Shorouk Molander, Gary A. Org Lett [Image: see text] An electrophilic, imide-based, visible-light-promoted photoredox/Ni-catalyzed cross-coupling reaction for the synthesis of aliphatic ketones has been developed. This protocol proceeds through N–C(O) bond activation, made possible through the lower activation energy for metal insertion into this bond due to delocalization of the lone pair of electrons on the nitrogen by electron-withdrawing groups. The operationally simple and mild cross-coupling reaction is performed at ambient temperature and exhibits tolerance for a variety of functional groups. American Chemical Society 2017-04-26 2017-05-05 /pmc/articles/PMC5423445/ /pubmed/28445061 http://dx.doi.org/10.1021/acs.orglett.7b00989 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Amani, Javad
Alam, Rauful
Badir, Shorouk
Molander, Gary A.
Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N–C Cleavage of Imides
title Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N–C Cleavage of Imides
title_full Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N–C Cleavage of Imides
title_fullStr Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N–C Cleavage of Imides
title_full_unstemmed Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N–C Cleavage of Imides
title_short Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N–C Cleavage of Imides
title_sort synergistic visible-light photoredox/nickel-catalyzed synthesis of aliphatic ketones via n–c cleavage of imides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5423445/
https://www.ncbi.nlm.nih.gov/pubmed/28445061
http://dx.doi.org/10.1021/acs.orglett.7b00989
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