Catalytic amounts of 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO)
are used in combination with
[bis(acetoxy)iodo]benzene (BAIB) as a stoichiometric oxidant in the
conversion of primary and
secondary alcohols to carbonyl compounds. This procedure works
efficiently at room temperature
in almost all common solvents and neat in some cases. This process
exhibits a very high degree of
selectivity for the oxidation of primary alcohols to aldehydes, without
any noticeable overoxidation
to carboxyl compounds, and a high chemoselectivity in the presence of
either secondary alcohols or
of other oxidizable moieties. This procedure allows an easy,
convenient, high-yielding method for
the oxidation of alcohols starting from commercially available
compounds.
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