Metal-Free Deoxygenation of Carbohydrates

The conversion of readily available cellulosic biomass to valuable feedstocks and fuels is an attrative goal but a challenging transformation that requires the cleavage of multiple nonactivated CO bonds. Herein, the Lewis acid trispentafluorophenylborane (B(C6F5)3) is shown to catalyze the metal‐fr...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2014-02, Vol.53 (6), p.1646-1649
Main Authors: Adduci, Laura L., McLaughlin, Matthew P., Bender, Trandon A., Becker, Jennifer J., Gagné, Michel R.
Format: Article
Language:English
Subjects:
Biomass
Carbohydrates
Deoxygenation
Hexanes
hydrosilylation
Lewis acid
Reduction
renewable feedstocks
Silanes
Transformations
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Summary:The conversion of readily available cellulosic biomass to valuable feedstocks and fuels is an attrative goal but a challenging transformation that requires the cleavage of multiple nonactivated CO bonds. Herein, the Lewis acid trispentafluorophenylborane (B(C6F5)3) is shown to catalyze the metal‐free hydrosilylative reduction of monosaccharides and polysaccharides to give hydrocarbons with reduced oxygen content. The choice of the silane reductant influences the degree of deoxygenation, with diethylsilane effecting the complete reduction to produce hexanes while tertiary silanes give partially deoxygenated tetraol and triol products. A spoonful of sugar: The Lewis acid B(C6F5)3 catalyzes the complete deoxygenation of carbohydrates to give a mixture of hexane and hexene isomers, with diethylsilane (Et2SiH2) providing the hydride equivalent. A variety of carbohydrates including methyl cellulose can be deoxygenated by this metal‐free method, and the system can be tuned for selective deoxygenation at certain sites.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201306864