Diarylmethyl ethers and Pd salts or complexes: a perfect combination for the protection and deprotection of alcohols |
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| Authors: | Yann Bikard Roufia Mezaache Jean-Marc Weibel Abdelhamid Benkouider Claude Sirlin Patrick Pale |
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| Institution: | aLaboratoire de synthèse et réactivité organiques, associé au CNRS, Institut de Chimie, Université L. Pasteur, 67000 Strasbourg, France;bLaboratoire de Chimie et Chimie de l'Environnement, Département de Chimie, Faculté des Sciences, Université de Batna, Batna 05000, Algeria;cLaboratoire de synthèses métallo-induites, associé au CNRS, Institut de Chimie, Université L. Pasteur, 67000 Strasbourg, France |
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| 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. |
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