A mild and efficient selective tetrahydropyranylation of primary alcohols and deprotection of THP ethers of phenols and alcohols using PdCl2(CH3CN)2 as catalyst

Primary alcohols were selectively tetrahydropyranylated in good to excellent yields at room temperature using PdCl2(CH3CN)2 as catalyst in tetrahydrofuran (THF) in the presence of phenols, secondary, and tertiary alcohols. The tetrahydropyranyl (THP) group could be efficiently removed using PdCl2(CH3CN)2 as catalyst in CH3CN, while other protection groups such as p-toluenesulfonyl (Ts), tert-butyldiphenylsilyl (TBDPS), benzyloxycarbonyl (Cbz), allyl, benzyl (Bn), and benzoyl (Bz) remained intact under these conditions.