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Zn-N(x) sites on N-doped carbon for aerobic oxidative cleavage and esterification of C(CO)-C bonds

Selective cleavage of C-C bonds is very important in organic chemistry, but remains challenging because of their inert chemical nature. Herein, we report that Zn/NC-X catalysts, in which Zn(2+) coordinate with N species on microporous N-doped carbon (NC) and X denotes the pyrolysis temperature, can...

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Autores principales: Xie, Chao, Lin, Longfei, Huang, Liang, Wang, Zixin, Jiang, Zhiwei, Zhang, Zehui, Han, Buxing
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8355145/
https://www.ncbi.nlm.nih.gov/pubmed/34376654
http://dx.doi.org/10.1038/s41467-021-25118-0
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author Xie, Chao
Lin, Longfei
Huang, Liang
Wang, Zixin
Jiang, Zhiwei
Zhang, Zehui
Han, Buxing
author_facet Xie, Chao
Lin, Longfei
Huang, Liang
Wang, Zixin
Jiang, Zhiwei
Zhang, Zehui
Han, Buxing
author_sort Xie, Chao
collection PubMed
description Selective cleavage of C-C bonds is very important in organic chemistry, but remains challenging because of their inert chemical nature. Herein, we report that Zn/NC-X catalysts, in which Zn(2+) coordinate with N species on microporous N-doped carbon (NC) and X denotes the pyrolysis temperature, can effectively catalyze aerobic oxidative cleavage of C(CO)-C bonds and quantitatively convert acetophenone to methyl benzoate with a yield of 99% at 100 °C. The Zn/NC-950 can be applied for a wide scope of acetophenone derivatives as well as more challenging alkyl ketones. Detail mechanistic investigations reveal that the catalytic performance of Zn/NC-950 can be attributed to the coordination between Zn(2+) and N species to change the electronic state of the metal, synergetic effect of the Zn single sites with their surrounding N atoms, as well as the microporous structure with the high surface area and structural defects of the NC.
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spelling pubmed-83551452021-08-30 Zn-N(x) sites on N-doped carbon for aerobic oxidative cleavage and esterification of C(CO)-C bonds Xie, Chao Lin, Longfei Huang, Liang Wang, Zixin Jiang, Zhiwei Zhang, Zehui Han, Buxing Nat Commun Article Selective cleavage of C-C bonds is very important in organic chemistry, but remains challenging because of their inert chemical nature. Herein, we report that Zn/NC-X catalysts, in which Zn(2+) coordinate with N species on microporous N-doped carbon (NC) and X denotes the pyrolysis temperature, can effectively catalyze aerobic oxidative cleavage of C(CO)-C bonds and quantitatively convert acetophenone to methyl benzoate with a yield of 99% at 100 °C. The Zn/NC-950 can be applied for a wide scope of acetophenone derivatives as well as more challenging alkyl ketones. Detail mechanistic investigations reveal that the catalytic performance of Zn/NC-950 can be attributed to the coordination between Zn(2+) and N species to change the electronic state of the metal, synergetic effect of the Zn single sites with their surrounding N atoms, as well as the microporous structure with the high surface area and structural defects of the NC. Nature Publishing Group UK 2021-08-10 /pmc/articles/PMC8355145/ /pubmed/34376654 http://dx.doi.org/10.1038/s41467-021-25118-0 Text en © The Author(s) 2021 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Xie, Chao
Lin, Longfei
Huang, Liang
Wang, Zixin
Jiang, Zhiwei
Zhang, Zehui
Han, Buxing
Zn-N(x) sites on N-doped carbon for aerobic oxidative cleavage and esterification of C(CO)-C bonds
title Zn-N(x) sites on N-doped carbon for aerobic oxidative cleavage and esterification of C(CO)-C bonds
title_full Zn-N(x) sites on N-doped carbon for aerobic oxidative cleavage and esterification of C(CO)-C bonds
title_fullStr Zn-N(x) sites on N-doped carbon for aerobic oxidative cleavage and esterification of C(CO)-C bonds
title_full_unstemmed Zn-N(x) sites on N-doped carbon for aerobic oxidative cleavage and esterification of C(CO)-C bonds
title_short Zn-N(x) sites on N-doped carbon for aerobic oxidative cleavage and esterification of C(CO)-C bonds
title_sort zn-n(x) sites on n-doped carbon for aerobic oxidative cleavage and esterification of c(co)-c bonds
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8355145/
https://www.ncbi.nlm.nih.gov/pubmed/34376654
http://dx.doi.org/10.1038/s41467-021-25118-0
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