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.
The reaction of 1H-2-phenyl-3-hydroxy-4-oxoquinoline (PhquinH(2); 1) with metallic copper leads to Cu(II)(PhquinH)(2) while in the presence of PPh(3) to Cu(I)(2)Cu(II)(Phquin)(2)(PPh(3))(4). In the presence of tmeda and O(2) ring cleavage occurs to give Cu(II)(tmeda)(PhquinH)(N-baa). Both reactions represent a mild N-H activation and an oxidative C-C bond scission.
Czaun
Miklós
M
Department of Organic Chemistry, University of Veszprém, 8201 Veszprém, Hungary.
Speier
Gábor
G
Párkányi
László
L