Metal-Free Deoxygenation of Carbohydrates

Authors

  • Laura L. Adduci,

    1. Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290 (USA)
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    • These authors contributed equally to this work.

  • Dr. Matthew P. McLaughlin,

    1. Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290 (USA)
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    • These authors contributed equally to this work.

  • Trandon A. Bender,

    1. Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290 (USA)
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  • Dr. Jennifer J. Becker,

    1. U.S. Army Research Office, P.O. Box 1221, Research Triangle Park, NC 27709 (USA)
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  • Prof. Dr. Michel R. Gagné

    Corresponding author
    1. Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290 (USA)
    • Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290 (USA)

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  • 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.

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[BOND]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.

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