(PhCH2PPh3)+Br3-: A versatile reagent for the preparation, deprotection, and oxidation of trimethylsilyl ethers

Abstract

Benzyltriphenylphosphonium tribromide (BTPTB), as a stable solid reagent, is easily prepared by the reaction of benzyltriphenylphosphonium bromide with Br2. This reagent can be used as an efficient catalyst for the conversion of alcohols to their corresponding trimethylsilyl ethers (TMS ethers) with hexamethyldisilazane (HMDS). Desilylation of TMS ethers is also catalyzed by BTPTB in MeOH at room temperature in high yields. BTPTB is also able to oxidize the TMS ethers to their corresponding carbonyl compounds in a mixture of MeOH/H2O in good to high yields. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.