Diarylmethyl ethers and Pd salts or complexes: a perfect combination for the protection and deprotection of alcohols

Abstract

Primary and secondary alcohols are easily protected as diphenylmethyl (DPM) or bis(methoxyphenyl)methyl (BMPM) ethers in good yield using PdCl2(CH3CN)2 as catalyst in dichloroethane at 60 or 20 °C, respectively. These conditions are compatible with other functional and protecting groups such as halides, esters, acetal, benzyl, para-methoxybenzyl, benzyloxycarbonyl, and tert-butyldiphenylsilyl. Good selectivity was observed in favor of primary over secondary alcohols. Deprotection of diphenylmethyl or bis(4-methoxyphenyl)methyl ethers was efficiently achieved at room temperature using PdCl2(CH3CN)2 in dichloroethane in the presence of 10 equiv of ethanol. © 2008 Elsevier Ltd. All rights reserved.