These authors contributed equally to this work.
Metal-Free Deoxygenation of Carbohydrates†
Article first published online: 13 JAN 2014
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 53, Issue 6, pages 1646–1649, February 3, 2014
How to Cite
Adduci, L. L., McLaughlin, M. P., Bender, T. A., Becker, J. J. and Gagné, M. R. (2014), Metal-Free Deoxygenation of Carbohydrates. Angew. Chem. Int. Ed., 53: 1646–1649. doi: 10.1002/anie.201306864
M.P.M. thanks the National Research Council for a postdoctoral fellowship, L.L.A. thanks the Progress Energy Foundation/UNC Institute for the Environment, M.R.G. thanks the Department of Energy (DE-FG02-05ER15630), and J.J.B. thanks the Army Research Office for funding.
- Issue published online: 3 FEB 2014
- Article first published online: 13 JAN 2014
- Manuscript Received: 5 AUG 2013
- Department of Energy. Grant Number: DE-FG02-05ER15630
- Army Research Office
- renewable feedstocks
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 CO 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.