Cargando…

Visible-light-driven Photocatalytic N-arylation of Imidazole Derivatives and Arylboronic Acids on Cu/graphene catalyst

N-aryl imidazoles play an important role as structural and functional units in many natural products and biologically active compounds. Herein, we report a photocatalytic route for the C-N cross-coupling reactions over a Cu/graphene catalyst, which can effectively catalyze N-arylation of imidazole a...

Descripción completa

Detalles Bibliográficos
Autores principales: Cui, Yan-Li, Guo, Xiao-Ning, Wang, Ying-Yong, Guo, Xiang-Yun
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4648406/
https://www.ncbi.nlm.nih.gov/pubmed/26189944
http://dx.doi.org/10.1038/srep12005
_version_ 1782401226634166272
author Cui, Yan-Li
Guo, Xiao-Ning
Wang, Ying-Yong
Guo, Xiang-Yun
author_facet Cui, Yan-Li
Guo, Xiao-Ning
Wang, Ying-Yong
Guo, Xiang-Yun
author_sort Cui, Yan-Li
collection PubMed
description N-aryl imidazoles play an important role as structural and functional units in many natural products and biologically active compounds. Herein, we report a photocatalytic route for the C-N cross-coupling reactions over a Cu/graphene catalyst, which can effectively catalyze N-arylation of imidazole and phenylboronic acid, and achieve a turnover frequency of 25.4 h(−1) at 25 (o)C and the irradiation of visible light. The enhanced catalytic activity of the Cu/graphene under the light irradiation results from the localized surface plasmon resonance of copper nanoparticles. The Cu/graphene photocatalyst has a general applicability for photocatalytic C-N, C-O and C-S cross-coupling of arylboronic acids with imidazoles, phenols and thiophenols. This study provides a green photocatalytic route for the production of N-aryl imidazoles.
format Online
Article
Text
id pubmed-4648406
institution National Center for Biotechnology Information
language English
publishDate 2015
publisher Nature Publishing Group
record_format MEDLINE/PubMed
spelling pubmed-46484062015-11-23 Visible-light-driven Photocatalytic N-arylation of Imidazole Derivatives and Arylboronic Acids on Cu/graphene catalyst Cui, Yan-Li Guo, Xiao-Ning Wang, Ying-Yong Guo, Xiang-Yun Sci Rep Article N-aryl imidazoles play an important role as structural and functional units in many natural products and biologically active compounds. Herein, we report a photocatalytic route for the C-N cross-coupling reactions over a Cu/graphene catalyst, which can effectively catalyze N-arylation of imidazole and phenylboronic acid, and achieve a turnover frequency of 25.4 h(−1) at 25 (o)C and the irradiation of visible light. The enhanced catalytic activity of the Cu/graphene under the light irradiation results from the localized surface plasmon resonance of copper nanoparticles. The Cu/graphene photocatalyst has a general applicability for photocatalytic C-N, C-O and C-S cross-coupling of arylboronic acids with imidazoles, phenols and thiophenols. This study provides a green photocatalytic route for the production of N-aryl imidazoles. Nature Publishing Group 2015-07-20 /pmc/articles/PMC4648406/ /pubmed/26189944 http://dx.doi.org/10.1038/srep12005 Text en Copyright © 2015, Macmillan Publishers Limited http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
spellingShingle Article
Cui, Yan-Li
Guo, Xiao-Ning
Wang, Ying-Yong
Guo, Xiang-Yun
Visible-light-driven Photocatalytic N-arylation of Imidazole Derivatives and Arylboronic Acids on Cu/graphene catalyst
title Visible-light-driven Photocatalytic N-arylation of Imidazole Derivatives and Arylboronic Acids on Cu/graphene catalyst
title_full Visible-light-driven Photocatalytic N-arylation of Imidazole Derivatives and Arylboronic Acids on Cu/graphene catalyst
title_fullStr Visible-light-driven Photocatalytic N-arylation of Imidazole Derivatives and Arylboronic Acids on Cu/graphene catalyst
title_full_unstemmed Visible-light-driven Photocatalytic N-arylation of Imidazole Derivatives and Arylboronic Acids on Cu/graphene catalyst
title_short Visible-light-driven Photocatalytic N-arylation of Imidazole Derivatives and Arylboronic Acids on Cu/graphene catalyst
title_sort visible-light-driven photocatalytic n-arylation of imidazole derivatives and arylboronic acids on cu/graphene catalyst
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4648406/
https://www.ncbi.nlm.nih.gov/pubmed/26189944
http://dx.doi.org/10.1038/srep12005
work_keys_str_mv AT cuiyanli visiblelightdrivenphotocatalyticnarylationofimidazolederivativesandarylboronicacidsoncugraphenecatalyst
AT guoxiaoning visiblelightdrivenphotocatalyticnarylationofimidazolederivativesandarylboronicacidsoncugraphenecatalyst
AT wangyingyong visiblelightdrivenphotocatalyticnarylationofimidazolederivativesandarylboronicacidsoncugraphenecatalyst
AT guoxiangyun visiblelightdrivenphotocatalyticnarylationofimidazolederivativesandarylboronicacidsoncugraphenecatalyst