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A Practical RuCl 3 -Catalyzed Oxidation Using Trichloroisocyanuric Acid As a Stoichiometric Oxidant under Mild Nonacidic Conditions

2004; American Chemical Society; Volume: 8; Issue: 6 Linguagem: Inglês

10.1021/op049940k

1520-586X

Hidenori Yamaoka, Narimasa Moriya, Masaya Ikunaka,

Synthesis and Catalytic Reactions

The combined use of catalytic RuCl3 (1.0 mol %) and stoichiometric trichloroisocyanuric acid (TCCA; 1.0 equiv) in the presence of n-Bu4NBr (2.0 mol %) and K2CO3 (3.0 equiv) in 1:1 MeCN/H2O at 25−45 °C allows smooth oxidation of primary alcohols to carboxylic acids. Secondary alcohols can be oxidized to ketones when using the same set of the reagents in 1:1 MeCN/H2O or 1:1 AcOEt/H2O. By proceeding under the nonacidic biphasic conditions dispensing with hazardous reagents, the oxidation reactions are applicable to structurally diverse alcohols, easy to work up, environmentally benign, and basically high-yielding.