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Oppenauer-type oxidation of secondary alcohols catalyzed by homogeneous water-soluble complexes1
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Oppenauer-type oxidation of secondary alcohols catalyzed by homogeneous water-soluble complexes1
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Journal Article
Oppenauer-type oxidation of secondary alcohols catalyzed by homogeneous water-soluble complexes1
2005
Overview
The catalytic system composed of [Ir(COD)Cl]^sub 2^, 2,2'-biquinoline-4,4'-dicarboxylic acid dipotassium salt (BQC), and sodium carbonate is highly efficient for the selective oxidation of benzylic, 1-heteroaromatic, aliphatic, and allylic secondary alcohols using catalyst:substrate ratios ranging from 0.4% to 2.5%. Sterically hindered allylic alcohols undergo selectively good conversions to the corresponding enones, while unhindered ones are completely isomerized to saturated ketones. Mercury tests indicate that the catalytic process is likely homogeneous. The mechanism proposed for this Oppenauer-type oxidation including the isomerization process is based on iridium-alkoxide species. [PUBLICATION ABSTRACT]
