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Issue 1, 2013
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Organocatalytic conversion of cellulose into a platform chemical

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The search for a source of fuels and chemicals that is both abundant and renewable has become of paramount importance. The polysaccharide cellulose meets both criteria, and methods have been developed for its transformation into the platform chemical 5-(hydroxymethyl)furfural (HMF). These methods typically employ harsh reaction conditions or toxic heavy metal catalysts, deterring large-scale implementation. Here, we describe a low-temperature, one-pot route that uses ortho-carboxyl-substituted phenylboronic acids as organocatalysts in conjunction with hydrated magnesium chloride and mineral acids to convert cellulose and cellulose-rich municipal waste to HMF in yields comparable to processes that use toxic heavy metal catalysts. Isotopic labeling studies indicate that the key aldose-to-ketose transformation occurs via an enediol intermediate. The route, which also allows for facile catalyst recovery and recycling, provides a green prototype for cellulose conversion.

Graphical abstract: Organocatalytic conversion of cellulose into a platform chemical

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Publication details

The article was received on 01 Sep 2012, accepted on 02 Oct 2012 and first published on 03 Oct 2012

Article type: Edge Article
DOI: 10.1039/C2SC21403B
Citation: Chem. Sci., 2013,4, 196-199
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    Organocatalytic conversion of cellulose into a platform chemical

    B. R. Caes, M. J. Palte and R. T. Raines, Chem. Sci., 2013, 4, 196
    DOI: 10.1039/C2SC21403B

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