Oxidative Cleavage of TBDMS Ether

Abstract

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.