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Paper | Regular issue | Vol 81, No. 11, 2010, pp.2539-2553
Published online, 6th September, 2010
DOI: 10.3987/COM-10-12027
Mild Oxidation of Alcohols Using Soluble Polymer-Supported TEMPO in Combination with Oxone: Effect of a Basic Matrix of TEMPO Derivatives

Kazutsugu Matsumoto,* Toshiaki Iwata, Masahiro Suenaga, Masayuki Okudomi, Masaki Nogawa, Mariko Nakano, Ai Sugahara, Yuta Bannai, and Kenji Baba

*Department of Chemistry, Meisei University, Hodokubo 2-1-1, Hino, Tokyo 191-8506, Japan

Abstract

The highly efficient and mild oxidation of alcohols using new soluble polymer-supported TEMPO derivatives in combination with Oxone is disclosed. Two types of the PEG-supported TEMPO derivative were easily synthesized by a simple esterification or Click Chemistry. The oxidation of primary alcohols with the precatalysts, TBAB, and Oxone in CH2Cl2 or BTF proceeded to afford the corresponding oxidized products. As a result of the reactions using several TEMPO derivatives including the nonpolymer-supported and insoluble polymer-supported compounds under the same reaction conditions, the synthesized PEG-supported TEMPO bearing a succinate spacer between the PEG and TEMPO parts was chosen as the best due to its high reactivity and product selectivity. This reaction was also applicable for the oxidation of secondary alcohols. In this system, the isolation of the products was achieved by simple filtration. The PEG-supported TEMPO bearing a succinate spacer was easily recovered and reused at least 10 times without a purification process.