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Highly effective and chemoselective hydrodeoxygenation of aromatic alcohols

Effective hydrodeoxygenation (HDO) of aromatic alcohols is very attractive in both conventional organic synthesis and upgrading of biomass-derived molecules, but the selectivity of this reaction is usually low because of the competitive hydrogenation of the unsaturated aromatic ring and the hydroxyl...

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Autores principales: Xu, Caiyun, Wu, Haihong, Zhang, Zhanrong, Zheng, Bingxiao, Zhai, Jianxin, Zhang, Kaili, Wu, Wei, Mei, Xuelei, He, Mingyuan, Han, Buxing
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8827088/
https://www.ncbi.nlm.nih.gov/pubmed/35282624
http://dx.doi.org/10.1039/d1sc06430d
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author Xu, Caiyun
Wu, Haihong
Zhang, Zhanrong
Zheng, Bingxiao
Zhai, Jianxin
Zhang, Kaili
Wu, Wei
Mei, Xuelei
He, Mingyuan
Han, Buxing
author_facet Xu, Caiyun
Wu, Haihong
Zhang, Zhanrong
Zheng, Bingxiao
Zhai, Jianxin
Zhang, Kaili
Wu, Wei
Mei, Xuelei
He, Mingyuan
Han, Buxing
author_sort Xu, Caiyun
collection PubMed
description Effective hydrodeoxygenation (HDO) of aromatic alcohols is very attractive in both conventional organic synthesis and upgrading of biomass-derived molecules, but the selectivity of this reaction is usually low because of the competitive hydrogenation of the unsaturated aromatic ring and the hydroxyl group. The high activity of noble metal-based catalysts often leads to undesired side reactions (e.g., saturation of the aromatic ring) and excessive hydrogen consumption. Non-noble metal-based catalysts suffer from unsatisfied activity and selectivity and often require harsh reaction conditions. Herein, for the first time, we report chemoselective HDO of various aromatic alcohols with excellent selectivity, using porous carbon–nitrogen hybrid material-supported Co catalysts. The C–OH bonds were selectively cleaved while leaving the aromatic moiety intact, and in most cases the yields of targeted compounds reached above 99% and the catalyst could be readily recycled. Nitrogen doping on the carbon skeleton of the catalyst support (C–N matrix) significantly improved the yield of the targeted product. The presence of large pores and a high surface area also improved the catalyst efficiency. This work opens the way for efficient and selective HDO reactions of aromatic alcohols using non-noble metal catalysts.
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spelling pubmed-88270882022-03-11 Highly effective and chemoselective hydrodeoxygenation of aromatic alcohols Xu, Caiyun Wu, Haihong Zhang, Zhanrong Zheng, Bingxiao Zhai, Jianxin Zhang, Kaili Wu, Wei Mei, Xuelei He, Mingyuan Han, Buxing Chem Sci Chemistry Effective hydrodeoxygenation (HDO) of aromatic alcohols is very attractive in both conventional organic synthesis and upgrading of biomass-derived molecules, but the selectivity of this reaction is usually low because of the competitive hydrogenation of the unsaturated aromatic ring and the hydroxyl group. The high activity of noble metal-based catalysts often leads to undesired side reactions (e.g., saturation of the aromatic ring) and excessive hydrogen consumption. Non-noble metal-based catalysts suffer from unsatisfied activity and selectivity and often require harsh reaction conditions. Herein, for the first time, we report chemoselective HDO of various aromatic alcohols with excellent selectivity, using porous carbon–nitrogen hybrid material-supported Co catalysts. The C–OH bonds were selectively cleaved while leaving the aromatic moiety intact, and in most cases the yields of targeted compounds reached above 99% and the catalyst could be readily recycled. Nitrogen doping on the carbon skeleton of the catalyst support (C–N matrix) significantly improved the yield of the targeted product. The presence of large pores and a high surface area also improved the catalyst efficiency. This work opens the way for efficient and selective HDO reactions of aromatic alcohols using non-noble metal catalysts. The Royal Society of Chemistry 2022-01-19 /pmc/articles/PMC8827088/ /pubmed/35282624 http://dx.doi.org/10.1039/d1sc06430d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Xu, Caiyun
Wu, Haihong
Zhang, Zhanrong
Zheng, Bingxiao
Zhai, Jianxin
Zhang, Kaili
Wu, Wei
Mei, Xuelei
He, Mingyuan
Han, Buxing
Highly effective and chemoselective hydrodeoxygenation of aromatic alcohols
title Highly effective and chemoselective hydrodeoxygenation of aromatic alcohols
title_full Highly effective and chemoselective hydrodeoxygenation of aromatic alcohols
title_fullStr Highly effective and chemoselective hydrodeoxygenation of aromatic alcohols
title_full_unstemmed Highly effective and chemoselective hydrodeoxygenation of aromatic alcohols
title_short Highly effective and chemoselective hydrodeoxygenation of aromatic alcohols
title_sort highly effective and chemoselective hydrodeoxygenation of aromatic alcohols
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8827088/
https://www.ncbi.nlm.nih.gov/pubmed/35282624
http://dx.doi.org/10.1039/d1sc06430d
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