Catalytic Hypervalent Iodine Oxidation Using 4-Iodophenoxyacetic Acid and Oxone^[○!R] : Oxidation of p-Alkoxyphenols to p-Benzoquinones

概要

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A catalytic hypervalent iodine oxidation of p-alkoxyphenols using 4-iodophenoxyacetic acid (1a) and Oxone^[○!R] was developed. Reaction of p-alkoxyphenol (2) with a catalytic amount of 1a in the presence of Oxone^[○!R] as a cooxidant in 2,2,2-trifluoroethanol-water (1:2) gave the corresponding p-quinone (3) in excellent yield without special operation. The substituent effect on iodobenzene ring in the oxidation was observed; p-alkoxy is the most effective, with the series following the approximate order p-RO>p-Me, o-MeO, m-MeO>H>o-CO_2H. And remarkable solvent effects were observed.
公益社団法人日本薬学会の論文
2009-03-01