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Synfacts 2014; 10(3): 0322
DOI: 10.1055/s-0033-1340721
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

α-Aminoxylation of Ketones with TEMPO Using Cu/SiO2-Fe

Contributor(s):
Yasuhiro Uozumi
,
Noboru Kobayashi
Xie Y.-X, Song R.-J, * Liu Y, Liu Y.-Y, Xiang J.-N, Li J.-H. * Hunan University, Changsha, P. R. of China
Copper-Catalyzed α-Aminoxylation of Ketones with 2,2,6,6-Tetramethylpiperidine-1-oxyl (TEMPO).

Adv. Synth. Catal. 2013;
355: 3387-3390
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Further Information

Publication History

Publication Date:
17 February 2014 (online)

 
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Key words

copper - iron - aminoxylation - ketones - TEMPO

Significance

Copper supported on SiO2-coated iron powder (Cu/SiO2-Fe) was prepared by mixing iron powder and tetraethoxysilane (TEOS) in a mixture of aqueous NH3–EtOH followed by treatment with aqueous copper sulfate (eq. 1). Cu/SiO2-Fe promoted the α-aminoxylation of 2-aryloxy- and 2-acetoxy-1-arylethanones with TEMPO to give the corresponding aminoxylated products in up to 99% yield (19 examples, eq. 2).


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Comment

In the aminoxylation of 2-phenoxy-1-phenylethanone, the catalyst was recovered by magnetic separation and reused seven times with a slight decrease of its catalytic activity (1st reuse: 90% yield; 7th reuse: 80% yield).


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