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

作者：Bikard Yann; Mezaache Roufia; Weibel Jean Marc; Benkouider Abdelhamid; Sirlin Claude; Pale Patrick^*

来源：Tetrahedron, 2008, 64(44): 10224-10232.

DOI：10.1016/j.tet.2008.08.026

Primary and secondary alcohols are easily protected as diphenylmethyl (DPM) or bis(methoxyphenyl)methyl (BMPM) ethers in good yield using PdCl(2)(CH(3)CN)(2) as catalyst in dichloroethane at 60 or 20 degrees C, respectively. These conditions are compatible with other functional and protecting groups such as halides, esters, acetal, benzyl, para-methoxybenzyl, benzyloxycarbonyl, and tert-butyldiphenylsilyt. 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 PdCl(2)(CH(3)CN)(2) in dichloroethane in the presence of 10 equiv of ethanol.

• 出版日期2008-10-27