Catalytic Selective Deoxygenation of Polyols Using the B(C6F5)3/Silane System

Abstract

The selective deoxygenation of polyols is an important frontier in our ability to transform biomass-derived compounds and other synthetic intermediates. In this Synpacts article, recent approaches using a B(C6F5)3/silane combination to site-selectively deoxygenate polyols are highlighted. First, the work of Gagne and coworkers is discussed. They developed a partial, selective deoxygenation of biologically sourced polyols proceeding through an elegant example of anchimeric assistance. In the second part, we present our recent work describing a catalytic deoxygenation of terminal diols with selectivity for the cleavage of the primary hydroxyl group. This transformation was enabled by the strategic formation of a cyclic siloxane intermediate. 1 Introduction 2 Background 3 Selective Deoxygenation of Carbohydrates 4 Selective Deoxygenation of Terminal Diols at the Primary Position 5 Conclusion