A collaborative project between the R. G. Bergman and J. A. Ellman research groups has led to a new method for the catalytic didehydroxylation of vicinal diols. Employing a readily available low-valent rhenium carbonyl complex and a simple alcohol as a reducing agent, both terminal and internal vicinal diols are deoxygenated to olefins in good yield. The optional addition of acid (TsOH, H2SO4) as additive provides access to lower reaction temperatures. This new system enables the transformation of a four-carbon sugar polyol into an oxygen-reduced compound, providing promising evidence for its practical application to produce unsaturated compounds from biomass-derived materials.

Toward greener routes to hydrocarbons: Deoxygenation of biomass-related polyols

243rd National Meeting (2012)

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