A Stable Palladium Catalyst for Polyol Oxidation CAS 959698-19-2

A Stable Palladium Catalyst for Polyol Oxidation CAS 959698-19-2

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Acetato(2,9-dimethyl-1,10-phenanthroline) palladium(II) dimer bis(trifluoromethanesulfonate), 99%) (46-0970) CAS 959698-19-2is an oxidation catalyst from the Waymouth Research Group at Stanford University. (shown below)1

Image1

The compound is useful as a catalyst for the chemo selective oxidation of polyols with yields from 60 to 88%.  Examples are given in the following equations.

Image2

The regio- and chemoselective oxidation of unprotected vicinal polyols occurs readily under mild reaction conditions. The oxidation of primary alcohols is preferred over secondary alcohols, while for vicinal diols oxidation is faster and more selective.  Vicinal 1,2-diols are oxidized selectively to hydroxy ketones, and oxidative lactonization of 1,5-diols yields cyclic lactones.   The catalyst loadings are as low as 0.12 mol % for reactions on a 10g scale.  The elegant selectivity of this catalyst system is demonstrated in the chemoselective and stereospecific oxidation of the polyol (S,S)-1,2,3,4-tetrahydroxybutane [(S,S)-threitol] to (S)-erythrulose.1

 

Reference:
1. J. Am. Chem. Soc., 2013, 135, 7593.

 

 

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