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

Dedicated to Prof. Erick M. Carreira

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 Gagné 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

Key words

deoxygenation - catalysis - silane - carbohydrates - diols

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