Deprotection Of Tert-butyldimethylsilyl Ethers Research Articles

Silica-coated Fe3O4 magnetic nanoparticles-supported sulfonic acid as a highly active and reusable catalyst in chemoselective deprotection of tert-butyldimethylsilyl (TBDMS) ethers

Anchored propyl sulfonic acid on the surface of silica-coated magnetic nanoparticles (Fe3O4@SiO2@PrSO3H) was successfully employed in the deprotection of TBDMS ethers. The prepared magnetically separable nanocatalyst exhibited efficient catalytic activity with high conversion and selectivity in cleavage of TBDMS ethers. TBDMS ethers are efficiently cleaved to the corresponding hydroxyl compounds in methanol solution containing 2 mol% magnetic nano-catalysts. Good to excellent yields of products, simple work-up and product separation, selective cleavage of TBDMS ethers in the presence of TBDPS ethers, easy recycling of the catalyst with external magnet with no loss in its activity (7 reaction cycles) are important features of this new protocol.

One-Pot Bi(OTf)3-Catalyzed Oxidative Deprotection of tert-Butyldimethyl Silyl Ethers with TEMPO and Co-Oxidants

A sequential one-pot synthesis for the oxidation of primary and secondary tert-butyldimethylsilyl (TBDMS) ethers, using catalytic amounts of metal triflates and TEMPO in combination with PhIO or PhI(OAc)2 in THF or acetonitrile, is described. Acid-sensitive protecting groups such as methylidene, isopropylidene, acetals, and Boc are unaffected under the reaction conditions. Another feature of this procedure is its high selectivity for TBDMS ethers over tert-butyldiphenylsilyl ethers and of aliphatic TBDMS groups over phenolic TBDMS groups.

A mild and efficient method for the selective cleavage of tert-butyldimethylsilyl ethers to alcohols

A mild and efficient method for the selective deprotection of primary allylic and homoallylic, primary benzylic and aryl tert-butyldimethylsilyl (TBDMS) ethers has been established using a combination of H 2O and DMSO at 90°C. All other primary and secondary TBDMS ethers remained unaffected under the reaction condition. The method is very effective in deprotection of TBDMS ethers in the presence of other sensitive functional groups.