Visible-light enabled room-temperature dealkylative imidation of secondary and tertiary amines promoted by aerobic ruthenium catalysis

Employing sulfonyl azide as a nitrogen donor, a visible-light-enabled aerobic dealkylative imidation of tertiary and secondary amines involving C(sp(3))–C(sp(3)) bond cleavage with moderate to excellent yields at room temperature is described. It has been demonstrated that this imidation could take...

Descripción completa

Detalles Bibliográficos
Autores principales: Yang, Dong, Shi, Jingqi, Chen, Jiaming, Jia, Xiaoqi, Shi, Cuiying, Ma, Lifang, Li, Ziyuan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9033495/
https://www.ncbi.nlm.nih.gov/pubmed/35478631
http://dx.doi.org/10.1039/d0ra10517a
_version_ 1784692903182860288
author Yang, Dong
Shi, Jingqi
Chen, Jiaming
Jia, Xiaoqi
Shi, Cuiying
Ma, Lifang
Li, Ziyuan
author_facet Yang, Dong
Shi, Jingqi
Chen, Jiaming
Jia, Xiaoqi
Shi, Cuiying
Ma, Lifang
Li, Ziyuan
author_sort Yang, Dong
collection PubMed
description Employing sulfonyl azide as a nitrogen donor, a visible-light-enabled aerobic dealkylative imidation of tertiary and secondary amines involving C(sp(3))–C(sp(3)) bond cleavage with moderate to excellent yields at room temperature is described. It has been demonstrated that this imidation could take place spontaneously upon visible-light irradiation, and could be facilitated considerably by a ruthenium photocatalyst and oxygen. An alternative mechanism to the previous aerobic photoredox pathway has also been proposed.
format Online
Article
Text
id pubmed-9033495
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-90334952022-04-26 Visible-light enabled room-temperature dealkylative imidation of secondary and tertiary amines promoted by aerobic ruthenium catalysis Yang, Dong Shi, Jingqi Chen, Jiaming Jia, Xiaoqi Shi, Cuiying Ma, Lifang Li, Ziyuan RSC Adv Chemistry Employing sulfonyl azide as a nitrogen donor, a visible-light-enabled aerobic dealkylative imidation of tertiary and secondary amines involving C(sp(3))–C(sp(3)) bond cleavage with moderate to excellent yields at room temperature is described. It has been demonstrated that this imidation could take place spontaneously upon visible-light irradiation, and could be facilitated considerably by a ruthenium photocatalyst and oxygen. An alternative mechanism to the previous aerobic photoredox pathway has also been proposed. The Royal Society of Chemistry 2021-05-25 /pmc/articles/PMC9033495/ /pubmed/35478631 http://dx.doi.org/10.1039/d0ra10517a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Yang, Dong
Shi, Jingqi
Chen, Jiaming
Jia, Xiaoqi
Shi, Cuiying
Ma, Lifang
Li, Ziyuan
Visible-light enabled room-temperature dealkylative imidation of secondary and tertiary amines promoted by aerobic ruthenium catalysis
title Visible-light enabled room-temperature dealkylative imidation of secondary and tertiary amines promoted by aerobic ruthenium catalysis
title_full Visible-light enabled room-temperature dealkylative imidation of secondary and tertiary amines promoted by aerobic ruthenium catalysis
title_fullStr Visible-light enabled room-temperature dealkylative imidation of secondary and tertiary amines promoted by aerobic ruthenium catalysis
title_full_unstemmed Visible-light enabled room-temperature dealkylative imidation of secondary and tertiary amines promoted by aerobic ruthenium catalysis
title_short Visible-light enabled room-temperature dealkylative imidation of secondary and tertiary amines promoted by aerobic ruthenium catalysis
title_sort visible-light enabled room-temperature dealkylative imidation of secondary and tertiary amines promoted by aerobic ruthenium catalysis
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9033495/
https://www.ncbi.nlm.nih.gov/pubmed/35478631
http://dx.doi.org/10.1039/d0ra10517a
work_keys_str_mv AT yangdong visiblelightenabledroomtemperaturedealkylativeimidationofsecondaryandtertiaryaminespromotedbyaerobicrutheniumcatalysis
AT shijingqi visiblelightenabledroomtemperaturedealkylativeimidationofsecondaryandtertiaryaminespromotedbyaerobicrutheniumcatalysis
AT chenjiaming visiblelightenabledroomtemperaturedealkylativeimidationofsecondaryandtertiaryaminespromotedbyaerobicrutheniumcatalysis
AT jiaxiaoqi visiblelightenabledroomtemperaturedealkylativeimidationofsecondaryandtertiaryaminespromotedbyaerobicrutheniumcatalysis
AT shicuiying visiblelightenabledroomtemperaturedealkylativeimidationofsecondaryandtertiaryaminespromotedbyaerobicrutheniumcatalysis
AT malifang visiblelightenabledroomtemperaturedealkylativeimidationofsecondaryandtertiaryaminespromotedbyaerobicrutheniumcatalysis
AT liziyuan visiblelightenabledroomtemperaturedealkylativeimidationofsecondaryandtertiaryaminespromotedbyaerobicrutheniumcatalysis

Ejemplares similares