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Synfacts 2008(1): 0104-0104  
DOI: 10.1055/s-2007-991459
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Oxidation by Polymer-Supported 2-Iodylphenol Ethers

Contributor(s): Yasuhiro Uozumi, Yohei Oe
R. R. Karimov, Z.-G. M. Kazhkenov, M. J. Modjewski, E. M. Peterson, V. V. Zhdankin*
University of Minnesota, Duluth, USA
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Publication History

Publication Date:
18 December 2007 (online)

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Significance

A new polymer-supported 2-iodyl­phenol ether was prepared and applied to the oxidation reactions of alcohols. Thus, 1-iodophenol 1 reacted with ethyl 4-bromobutanoate in the presence of K2CO3 to give the ester 2. The saponification of 2 with LiOH, followed by the reduction with BH3·Me2S afforded alcohol 3. The alcohol 3 was treated with NaH in DMF and then with Merrifield resin in the presence of KI to give the polymeric 2-iodophenyl ether 4. The polymer-supported 2-iodylphenol ether 5 was provided by the oxidation of 4 with oxone in the presence of NaHCO3 (eq. 1). The oxidation reactions of various alcohols with one equivalent of 5 in refluxed DME afforded the corresponding carbonyl compounds in 77% to >99% yield (eq. 2).