Biomass Transformation of Cellulose via N-Heterocyclic Carbene-Catalyzed Umpolung of 5-(Chloromethyl)furfural
Summary: Nature produces ∼170 billion tons of biomass per year; meanwhile, only a small percentage is used. Cellulose is the most abundant component in biomass; thus, the selective transformation of cellulose to high-value-added products is one of the most promising pathways to sustainable society....
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doaj-cc606f3978aa408a937ad15f5ecfe2352020-11-25T04:09:03ZengElsevierCell Reports Physical Science2666-38642020-06-0116100071Biomass Transformation of Cellulose via N-Heterocyclic Carbene-Catalyzed Umpolung of 5-(Chloromethyl)furfuralLei Dai0Ye Qiu1Yuan-Yuan Xu2Song Ye3Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China; University of Chinese Academy of Sciences, Beijing 100049, ChinaBeijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China; University of Chinese Academy of Sciences, Beijing 100049, ChinaBeijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China; University of Chinese Academy of Sciences, Beijing 100049, ChinaBeijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China; University of Chinese Academy of Sciences, Beijing 100049, China; Corresponding authorSummary: Nature produces ∼170 billion tons of biomass per year; meanwhile, only a small percentage is used. Cellulose is the most abundant component in biomass; thus, the selective transformation of cellulose to high-value-added products is one of the most promising pathways to sustainable society. Here, we report an N-heterocyclic carbene-catalyzed umpolung of 5-(chloromethyl)furfural, which is easily obtained from cellulose, and its subsequent reaction with ketones is developed, giving the corresponding highly functionalized products in good yields. We believe that this carbene-catalyzed transformation of 5-(chloromethyl)furfural will facilitate the development of biomass transformations.http://www.sciencedirect.com/science/article/pii/S2666386420300667biomasscellulose5-(chloromethyl)furfuralN-heterocyclic carbeneε-umpolungOrganocatalysis |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Lei Dai Ye Qiu Yuan-Yuan Xu Song Ye |
spellingShingle |
Lei Dai Ye Qiu Yuan-Yuan Xu Song Ye Biomass Transformation of Cellulose via N-Heterocyclic Carbene-Catalyzed Umpolung of 5-(Chloromethyl)furfural Cell Reports Physical Science biomass cellulose 5-(chloromethyl)furfural N-heterocyclic carbene ε-umpolung Organocatalysis |
author_facet |
Lei Dai Ye Qiu Yuan-Yuan Xu Song Ye |
author_sort |
Lei Dai |
title |
Biomass Transformation of Cellulose via N-Heterocyclic Carbene-Catalyzed Umpolung of 5-(Chloromethyl)furfural |
title_short |
Biomass Transformation of Cellulose via N-Heterocyclic Carbene-Catalyzed Umpolung of 5-(Chloromethyl)furfural |
title_full |
Biomass Transformation of Cellulose via N-Heterocyclic Carbene-Catalyzed Umpolung of 5-(Chloromethyl)furfural |
title_fullStr |
Biomass Transformation of Cellulose via N-Heterocyclic Carbene-Catalyzed Umpolung of 5-(Chloromethyl)furfural |
title_full_unstemmed |
Biomass Transformation of Cellulose via N-Heterocyclic Carbene-Catalyzed Umpolung of 5-(Chloromethyl)furfural |
title_sort |
biomass transformation of cellulose via n-heterocyclic carbene-catalyzed umpolung of 5-(chloromethyl)furfural |
publisher |
Elsevier |
series |
Cell Reports Physical Science |
issn |
2666-3864 |
publishDate |
2020-06-01 |
description |
Summary: Nature produces ∼170 billion tons of biomass per year; meanwhile, only a small percentage is used. Cellulose is the most abundant component in biomass; thus, the selective transformation of cellulose to high-value-added products is one of the most promising pathways to sustainable society. Here, we report an N-heterocyclic carbene-catalyzed umpolung of 5-(chloromethyl)furfural, which is easily obtained from cellulose, and its subsequent reaction with ketones is developed, giving the corresponding highly functionalized products in good yields. We believe that this carbene-catalyzed transformation of 5-(chloromethyl)furfural will facilitate the development of biomass transformations. |
topic |
biomass cellulose 5-(chloromethyl)furfural N-heterocyclic carbene ε-umpolung Organocatalysis |
url |
http://www.sciencedirect.com/science/article/pii/S2666386420300667 |
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