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DOI: 10.1055/s-2007-968295
Macroporous Polystyrene-Supported (Diacetoxyiodo)benzene
Y. Shang, T. Y. S. But, H. Togo*, P. H. Toy*
Chiba University, Japan and The University of Hong Kong, P. R. of China
Publication History
Publication Date:
23 March 2007 (online)
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Significance
Macroporous polystyrene-supported (diacetoxyiodo)benzene was prepared and applied to the oxidation of various organic functional groups. The iodination of macroporous polystyrene 1 with I2, I2O5, and H2SO4 gave polymer-supported iodobenzene 2, and the oxidation of the resulting iodobenzene 2 with Ac2O and H2O2 gave polymer-supported (diacetoxyiodo)benzene 3 (eq. 1). The oxidation of the primary and secondary alcohols took place in the presence of (diacetoxyiodo)benzene 3 and TEMPO to give aldehydes, carboxylic acids, and ketones in 83-96% yield (eq. 2-4). The oxidation of the dihydroquinone derivatives, diethyl 1,2-hydrazinedicarboxylate, Ph2S, Ph3P, and Ph3As also proceeded to give the corresponding oxidized products in 92-96% yield (eq. 5 and 6).