Heterocycles p. 2539 - 2553 (2010)
Update date:2022-08-31
Topics:
Matsumoto, Kazutsugu
Iwata, Toshiaki
Suenaga, Masahiro
Okudomi, Masayuki
Nogawa, Masaki
Nakano, Mariko
Sugahara, Ai
Bannai, Yuta
Baba, Kenji
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. The Japan Institute of Heterocyclic Chemistry.
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