Direct AlCl₃-catalyzed transformation of benzyl THP ethers and allyl benzyl ethers

THP and allyl groups are frequently used for the protection of alcohols. In this study, novel direct transformations of benzyl THP ethers and allyl benzyl ethers, protected forms of alcohols, are reported. TMSN₃ and AlCl₃ were employed as key azide reagent and catalyst to perform direct conversion of benzyl THP ethers and allyl benzyl ethers to azido compounds. In addition, direct nucleophile additions of carbon nucleophiles to benzyl THP ethers and allyl benzyl ethers were successfully accomplished in the presence of catalytic AlCl₃. The results indicate that this novel method could be applied to various direct transformations of benzyl THP ethers and allyl benzyl ethers such as azidation, allylation, and alkynylation.