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Metal-free Deoxygenation of Carbohydrates

Laura L Adduci, Matthew P McLaughlin, Trandon A Bender, Jennifer J Becker, Michel R Gagné

Angew Chem Int Ed Engl. 2014 Feb 3;53(6):1646-9.

PMID: 24492972

Abstract:

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(C6 F5 )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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP542916 Diethylsilane Diethylsilane 542-91-6 Price
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