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Synfacts 2006(4): 0406-0406  
DOI: 10.1055/s-2006-932094
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Polymeric N-(2-Iodyl-phenyl)-acylamide Reagent for Oxidation of Alcohols

Contributor(s): Yasuhiro Uozumi, Ray Kawade, Toshimasa Suzuka
U. Ladziata, J. Willging, V. V. Zhdankin*
University of Minnesota Duluth, USA
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Publication History

Publication Date:
24 March 2006 (online)

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Significance

Polymer-supported N-(2-iodyl-phenyl)-acylamide (NIPA resin 4) was prepared in three steps starting from 2-iodoaniline (1). It reacted with glutaric anhydride to give carboxylic acid 2. Resin 3 was prepared by HOBt/DIC-mediated amide bond formation between carboxylic acid 2 and aminomethylpolystyrene. The oxidation of resin 3 was carried out by an equimolar mixture of tetrabutylammonium oxone with methanesulfonic acid to give the NIPA resin 4 with good loading levels (0.7-0.8 mmol/g). The oxidation of alcohols took place in the presence of NIPA resin 4 in 1,2-dichloroethane to give the corresponding aldehydes or ketones (20 examples, 61-99% yields).