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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Rhenium-catalyzed didehydroxylation of vicinal diols to alkenes using a simple alcohol as a reducing agent
Elena Arceo1, Jonathan A Ellman, Robert G Bergman
1Department of Chemistry, University of California, and Division of Chemical Sciences, Lawrence Berkeley National Laboratory, Berkeley, California 94720, USA.
Abstract:
A new method for the catalytic didehydroxylation of vicinal diols is described. 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, H(2)SO(4)) 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.
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