Issue 8, 2004
From the journal:

Chemical Communications

Facile copper-mediated activation of the N–H bond and the oxidative cleavage of the C2–C3 bond in 1H-2-phenyl-3-hydroxy-4-oxoquinoline

Miklós Czaun,a   Gábor Speier*ab  and  László Párkányic  

* Corresponding authors

a Department of Organic Chemistry, University of Veszprém, 8201 Veszprém, Hungary
E-mail: speier@almos.vein.hu
Fax: +36 88 427 492
Tel: +36 88 422 022/4657

b Research Group for Petrochemistry, Hungarian Academy of Sciences, 8201 Veszprém, Hungary

c Hungarian Academy of Sciences, Chemical Research Center, Institute of Chemistry, H-1051 Budapest, Hungary

Abstract

The reaction of 1H-2-phenyl-3-hydroxy-4-oxoquinoline (PhquinH2; 1) with metallic copper leads to CuII(PhquinH)2 while in the presence of PPh3 to CuI2CuII(Phquin)2(PPh3)4. In the presence of tmeda and O2 ring cleavage occurs to give CuII(tmeda)(PhquinH)(N-baa). Both reactions represent a mild N–H activation and an oxidative C–C bond scission.

Graphical abstract: Facile copper-mediated activation of the N–H bond and the oxidative cleavage of the C2–C3 bond in 1H-2-phenyl-3-hydroxy-4-oxoquinoline

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Article information

DOI
https://doi.org/10.1039/B315919A
Article type
Communication
Submitted
05 Dec 2003
Accepted
02 Mar 2004
First published
18 Mar 2004

Chem. Commun., 2004, 1004-1005

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Facile copper-mediated activation of the N–H bond and the oxidative cleavage of the C2–C3 bond in 1H-2-phenyl-3-hydroxy-4-oxoquinoline

M. Czaun, G. Speier and L. Párkányi, Chem. Commun., 2004, 1004 DOI: 10.1039/B315919A

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