Electrochemical Umpolung of Bromide: Transition-Metal-Free Bromination of Indole C–H Bond

A facile and sustainable electrochemical umpolung of bromide ion protocol was developed under mild reaction conditions. Transition metal catalysts and exogenous chemical oxidants were obviated for the bromination of C–H bond. Notably, graphite rod, which is commercially available at supermarkets and...

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Detalles Bibliográficos
Autores principales: Zhang, Pan, Chen, Jianbin, Gao, Wei, Xiao, Yiting, Liu, Changwei, Xu, Shanghui, Yan, Xiaoli, Qin, Dawei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6412264/
https://www.ncbi.nlm.nih.gov/pubmed/30769954
http://dx.doi.org/10.3390/molecules24040696
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author Zhang, Pan
Chen, Jianbin
Gao, Wei
Xiao, Yiting
Liu, Changwei
Xu, Shanghui
Yan, Xiaoli
Qin, Dawei
author_facet Zhang, Pan
Chen, Jianbin
Gao, Wei
Xiao, Yiting
Liu, Changwei
Xu, Shanghui
Yan, Xiaoli
Qin, Dawei
author_sort Zhang, Pan
collection PubMed
description A facile and sustainable electrochemical umpolung of bromide ion protocol was developed under mild reaction conditions. Transition metal catalysts and exogenous chemical oxidants were obviated for the bromination of C–H bond. Notably, graphite rod, which is commercially available at supermarkets and is inexpensive, was employed as the electrode material. This operationally easy and environmentally friendly approach accomplished the synthesis of 3-bromoindole in excellent yield and regioselectivity.
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spelling pubmed-64122642019-04-09 Electrochemical Umpolung of Bromide: Transition-Metal-Free Bromination of Indole C–H Bond Zhang, Pan Chen, Jianbin Gao, Wei Xiao, Yiting Liu, Changwei Xu, Shanghui Yan, Xiaoli Qin, Dawei Molecules Communication A facile and sustainable electrochemical umpolung of bromide ion protocol was developed under mild reaction conditions. Transition metal catalysts and exogenous chemical oxidants were obviated for the bromination of C–H bond. Notably, graphite rod, which is commercially available at supermarkets and is inexpensive, was employed as the electrode material. This operationally easy and environmentally friendly approach accomplished the synthesis of 3-bromoindole in excellent yield and regioselectivity. MDPI 2019-02-15 /pmc/articles/PMC6412264/ /pubmed/30769954 http://dx.doi.org/10.3390/molecules24040696 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Zhang, Pan
Chen, Jianbin
Gao, Wei
Xiao, Yiting
Liu, Changwei
Xu, Shanghui
Yan, Xiaoli
Qin, Dawei
Electrochemical Umpolung of Bromide: Transition-Metal-Free Bromination of Indole C–H Bond
title Electrochemical Umpolung of Bromide: Transition-Metal-Free Bromination of Indole C–H Bond
title_full Electrochemical Umpolung of Bromide: Transition-Metal-Free Bromination of Indole C–H Bond
title_fullStr Electrochemical Umpolung of Bromide: Transition-Metal-Free Bromination of Indole C–H Bond
title_full_unstemmed Electrochemical Umpolung of Bromide: Transition-Metal-Free Bromination of Indole C–H Bond
title_short Electrochemical Umpolung of Bromide: Transition-Metal-Free Bromination of Indole C–H Bond
title_sort electrochemical umpolung of bromide: transition-metal-free bromination of indole c–h bond
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6412264/
https://www.ncbi.nlm.nih.gov/pubmed/30769954
http://dx.doi.org/10.3390/molecules24040696
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