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Potential-tuned selective electrosynthesis of azoxy-, azo- and amino-aromatics over a CoP nanosheet cathode

Azoxy-, azo- and amino-aromatics are among the most widely used building blocks in materials science pharmaceuticals and synthetic chemistry, but their controllable and green synthesis has not yet been well established. Herein, a facile potential-tuned electrosynthesis of azoxy-, azo- and amino-arom...

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Autores principales: Chong, Xiaodan, Liu, Cuibo, Huang, Yi, Huang, Chenqi, Zhang, Bin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Oxford University Press 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8288891/
https://www.ncbi.nlm.nih.gov/pubmed/34692044
http://dx.doi.org/10.1093/nsr/nwz146
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author Chong, Xiaodan
Liu, Cuibo
Huang, Yi
Huang, Chenqi
Zhang, Bin
author_facet Chong, Xiaodan
Liu, Cuibo
Huang, Yi
Huang, Chenqi
Zhang, Bin
author_sort Chong, Xiaodan
collection PubMed
description Azoxy-, azo- and amino-aromatics are among the most widely used building blocks in materials science pharmaceuticals and synthetic chemistry, but their controllable and green synthesis has not yet been well established. Herein, a facile potential-tuned electrosynthesis of azoxy-, azo- and amino-aromatics via aqueous selective reduction of nitroarene feedstocks over a CoP nanosheet cathode is developed. A series of azoxy-, azo- and amino-compounds with excellent selectivity, good functional group tolerance and high yields are produced by applying different bias input. The synthetically significant and challenging asymmetric azoxy-aromatics can be controllably synthesized in moderate to good yields. The use of water as the hydrogen source makes this strategy remarkably fascinating and promising. In addition, deuterated aromatic amines with a high deuterium content can be readily obtained by using D(2)O. By pairing with anodic oxidation of aliphatic amines to nitriles, synthetically useful building blocks can be simultaneously produced in a CoP||Ni(2)P two-electrode electrolyzer. Only 1.25 V is required to achieve a current density of 20 mA cm(−2), which is much lower than that of overall water splitting (1.70 V). The paired oxidation and reduction reactions can also be driven using a 1.5 V battery to synthesize nitrile and azoxybenzene with good yields and selectivity, further emphasizing the flexibility and controllability of our method. This work paves the way for a promising approach to the green synthesis of valuable chemicals through potential-controlled electrosynthesis.
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spelling pubmed-82888912021-10-21 Potential-tuned selective electrosynthesis of azoxy-, azo- and amino-aromatics over a CoP nanosheet cathode Chong, Xiaodan Liu, Cuibo Huang, Yi Huang, Chenqi Zhang, Bin Natl Sci Rev Research Article Azoxy-, azo- and amino-aromatics are among the most widely used building blocks in materials science pharmaceuticals and synthetic chemistry, but their controllable and green synthesis has not yet been well established. Herein, a facile potential-tuned electrosynthesis of azoxy-, azo- and amino-aromatics via aqueous selective reduction of nitroarene feedstocks over a CoP nanosheet cathode is developed. A series of azoxy-, azo- and amino-compounds with excellent selectivity, good functional group tolerance and high yields are produced by applying different bias input. The synthetically significant and challenging asymmetric azoxy-aromatics can be controllably synthesized in moderate to good yields. The use of water as the hydrogen source makes this strategy remarkably fascinating and promising. In addition, deuterated aromatic amines with a high deuterium content can be readily obtained by using D(2)O. By pairing with anodic oxidation of aliphatic amines to nitriles, synthetically useful building blocks can be simultaneously produced in a CoP||Ni(2)P two-electrode electrolyzer. Only 1.25 V is required to achieve a current density of 20 mA cm(−2), which is much lower than that of overall water splitting (1.70 V). The paired oxidation and reduction reactions can also be driven using a 1.5 V battery to synthesize nitrile and azoxybenzene with good yields and selectivity, further emphasizing the flexibility and controllability of our method. This work paves the way for a promising approach to the green synthesis of valuable chemicals through potential-controlled electrosynthesis. Oxford University Press 2020-02 2019-10-01 /pmc/articles/PMC8288891/ /pubmed/34692044 http://dx.doi.org/10.1093/nsr/nwz146 Text en © The Author(s) 2019. Published by Oxford University Press on behalf of China Science Publishing & Media Ltd. https://creativecommons.org/licenses/by/4.0/This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) ), which permits unrestricted reuse, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Article
Chong, Xiaodan
Liu, Cuibo
Huang, Yi
Huang, Chenqi
Zhang, Bin
Potential-tuned selective electrosynthesis of azoxy-, azo- and amino-aromatics over a CoP nanosheet cathode
title Potential-tuned selective electrosynthesis of azoxy-, azo- and amino-aromatics over a CoP nanosheet cathode
title_full Potential-tuned selective electrosynthesis of azoxy-, azo- and amino-aromatics over a CoP nanosheet cathode
title_fullStr Potential-tuned selective electrosynthesis of azoxy-, azo- and amino-aromatics over a CoP nanosheet cathode
title_full_unstemmed Potential-tuned selective electrosynthesis of azoxy-, azo- and amino-aromatics over a CoP nanosheet cathode
title_short Potential-tuned selective electrosynthesis of azoxy-, azo- and amino-aromatics over a CoP nanosheet cathode
title_sort potential-tuned selective electrosynthesis of azoxy-, azo- and amino-aromatics over a cop nanosheet cathode
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8288891/
https://www.ncbi.nlm.nih.gov/pubmed/34692044
http://dx.doi.org/10.1093/nsr/nwz146
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