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Synfacts 2008(12): 1349-1349  
DOI: 10.1055/s-0028-1083555
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

TEMPO-Immobilized on Magnetic C/Co Nanoparticles for Alcohol Oxidation

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Hidetoshi Ohta
A. Schätz, R. N. Grass, W. J. Stark*, O. Reiser*
Universität Regensburg, Germany and ETH Zürich, Switzerland
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Publikationsdatum:
20. November 2008 (online)

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Significance

The magnetic carbon (shell)/cobalt (core) (C/Co) nanoparticles immobilized TEMPO (CoNP-TEMPO) was prepared having in view its use the oxidation of primary alcohols 5 to the corresponding aldehydes 6 with NaOCl as a terminal oxidant. Thus, the reaction of C/Co NP with the in situ generated diazonium salt of 1 gave the functionalized C/Co NP 2. Then, 2 was converted into the (azidomethyl)phenyl derivative 3 using Mitsunobu reaction. Cu(I)-catalyzed 1,3-cycloaddition of 3 with propargyl ether TEMPO 4 afforded the CoNP-TEMPO catalyst. The oxidation of primary alcohols 5 with NaOCl was carried out in the presence of CoNP-TEMPO to give the corresponding aldehydes 6 (7 examples, 77-96% yield).