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Issue 48, 2015
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A chemoselective α-aminoxylation of aryl ketones: a cross dehydrogenative coupling reaction catalysed by Bu4NI

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Abstract

Tetrabutyl ammonium iodide (TBAI) catalyzed α-aminoxylation of ketones using aq. TBHP as an oxidant has been accomplished. We have shown that the CDC (cross dehydrogenative coupling) reactions of ketones with N-hydroxyimidates such as N-hydroxysuccinimide (NHSI), N-hydroxyphthalimide (NHPI), N-hydroxybenzotriazole (HOBt) and 1-hydroxy-7-azabenzotriazole (HOAt) lead to the corresponding oxygenated products in good to moderate yields. The application of this method has been demonstrated by transforming a few coupled products into synthetically useful intermediates and products.

Graphical abstract: A chemoselective α-aminoxylation of aryl ketones: a cross dehydrogenative coupling reaction catalysed by Bu4NI

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Supplementary files

Article information


Submitted
16 Sep 2015
Accepted
07 Oct 2015
First published
08 Oct 2015

Org. Biomol. Chem., 2015,13, 11651-11656
Article type
Paper
Author version available

A chemoselective α-aminoxylation of aryl ketones: a cross dehydrogenative coupling reaction catalysed by Bu4NI

Y. Siddaraju and K. R. Prabhu, Org. Biomol. Chem., 2015, 13, 11651 DOI: 10.1039/C5OB01929J

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