Catalytic aerobic oxidation of substituted 8-methylquinolines in PdII-2,6-pyridinedicarboxylic acid systems

被引:117
作者
Zhang, Jing [1 ]
Khaskin, Eugene [1 ]
Anderson, Nicholas P. [1 ]
Zavalij, Peter Y. [1 ]
Vedernikov, Andrei N. [1 ]
机构
[1] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA
关键词
D O I
10.1039/b803156h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The ability of Pd-II complexes derived from 2,6-pyridinedicarboxylic acids to catalyze homogeneous regioselective aerobic oxidation of 5- and 6-substituted8-methylquinolines in AcOH-Ac2O solution to produce corresponding 8-quinolylmethyl acetates in high yield was demonstrated; corresponding 8-quinoline carboxylic acids are minor reaction products.
引用
收藏
页码:3625 / 3627
页数:3
相关论文
共 25 条
[1]   OXYGENATION OF CYCLOPALLADATED N,N-DIMETHYLBENZYLAMINE COMPLEXES BY INORGANIC AND ORGANIC PEROXIDES - OXYGEN INSERTION INTO THE PALLADIUM-CARBON BOND [J].
ALSTERS, PL ;
TEUNISSEN, HT ;
BOERSMA, J ;
SPEK, AL ;
VANKOTEN, G .
ORGANOMETALLICS, 1993, 12 (11) :4691-4696
[2]  
[Anonymous], 2005, HDB C H TRANSFORMATI
[3]   DIBENZO[A,E]CYCLOOCTATETRAENE IN A PROPOSED TEST FOR HETEROGENEITY IN CATALYSTS FORMED FROM SOLUBLE PLATINUM GROUP METAL-COMPLEXES [J].
ANTON, DR ;
CRABTREE, RH .
ORGANOMETALLICS, 1983, 2 (07) :855-859
[4]   Carbon-oxygen bond formation at organopalladium centers:: The reactions of PdMeR(L2) (R = Me, 4-tolyl; L2= tmeda, bpy) with diaroyl peroxides and the involvement of organopalladium(IV) species [J].
Canty, AJ ;
Denney, MC ;
Skelton, BW ;
White, AH .
ORGANOMETALLICS, 2004, 23 (05) :1122-1131
[5]   Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].
Chen, Xiao ;
Hao, Xue-Shi ;
Goodhue, Charles E. ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791
[6]   Aerobic alcohol oxidation with cationic palladium complexes: insights into catalyst design and decomposition [J].
Conley, Nicholas R. ;
Labios, Liezel A. ;
Pearson, David M. ;
McCrory, Charles C. L. ;
Waymouth, Robert M. .
ORGANOMETALLICS, 2007, 26 (23) :5447-5453
[7]   Regioselective functionalization of unreactive carbon-hydrogen bonds [J].
Daugulis, Olafs ;
Zaitsev, Vladimir G. ;
Shabashov, Dmitry ;
Pham, Quynh-Nhu ;
Lazareva, Anna .
SYNLETT, 2006, (20) :3382-3388
[8]   Insertion of molecular oxygen into a palladium(II) hydride bond [J].
Denney, MC ;
Smythe, NA ;
Cetto, KL ;
Kemp, RA ;
Goldberg, KI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) :2508-2509
[9]   Reactions of hypervalent iodine reagents with palladium: Mechanisms and applications in organic synthesis [J].
Deprez, Nicholas R. ;
Sanford, Melanie S. .
INORGANIC CHEMISTRY, 2007, 46 (06) :1924-1935
[10]   Transition metal catalyzed oxidative functionalization of carbon-hydrogen bonds [J].
Dick, AR ;
Sanford, MS .
TETRAHEDRON, 2006, 62 (11) :2439-2463