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.
Key words
bismuth(III) triflate - carbonyl compounds - oxidation - silyl ethers - TEMPO
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