Elaboration of the ether cleaving ability and selectivity of the classical Pearlman's catalyst [Pd(OH)2/C]: concise synthesis of a precursor for a myo-inositol pyrophosphate

Abstract

The cleavage of propargyl, allyl, benzyl, and PMB ethers by Pd(OH)2/C can be tuned in that order, by varying the reaction conditions. Other moieties such as C–C double bonds, esters, trityl ether, p-bromo and p-nitrobenzyl ethers are stable to these reaction conditions. Cleavage of allyl ethers can be made catalytic by using 1:1 mixture of Pd(OH)2/C and Pd/C. The synthetic potential of the selective ether cleaving ability of Pd(OH)2/C, essentially under neutral conditions, has been demonstrated by an efficient synthesis of a precursor for the preparation of an inositol pyrophosphate derivative.