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(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.
Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290 (USA).
Laura L
LL
Adduci
Matthew P
MP
McLaughlin
Trandon A
TA
Bender
Jennifer J
JJ
Becker
Michel R
MR
Gagné
biomass; carbohydrates; deoxygenation; hydrosilylation; renewable feedstocks