Macroporous Polystyrene-Supported (Diacetoxyiodo)benzene

Y. Shang; T. Y. S. But; H. Togo; P. H. Toy

doi:10.1055/s-2007-968295

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Synfacts 2007(4): 0443-0443
DOI: 10.1055/s-2007-968295

Polymer-Supported Synthesis

Macroporous Polystyrene-Supported (Diacetoxyiodo)benzene

Contributor(s): Yasuhiro Uozumi, Tsutomu Kimura
Y. Shang, T. Y. S. But, H. Togo*, P. H. Toy*
Chiba University, Japan and The University of Hong Kong, P. R. of China

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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).