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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Main Authors:	Lei Dai, Ye Qiu, Yuan-Yuan Xu, Song Ye
Format:	Article
Language:	English
Published:	Elsevier 2020-06-01
Series:	Cell Reports Physical Science
Subjects:	biomass cellulose 5-(chloromethyl)furfural N-heterocyclic carbene ε-umpolung Organocatalysis
Online Access:	http://www.sciencedirect.com/science/article/pii/S2666386420300667

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spelling	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
work_keys_str_mv	AT leidai biomasstransformationofcellulosevianheterocycliccarbenecatalyzedumpolungof5chloromethylfurfural AT yeqiu biomasstransformationofcellulosevianheterocycliccarbenecatalyzedumpolungof5chloromethylfurfural AT yuanyuanxu biomasstransformationofcellulosevianheterocycliccarbenecatalyzedumpolungof5chloromethylfurfural AT songye biomasstransformationofcellulosevianheterocycliccarbenecatalyzedumpolungof5chloromethylfurfural
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Biomass Transformation of Cellulose via N-Heterocyclic Carbene-Catalyzed Umpolung of 5-(Chloromethyl)furfural

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