Mechanistic Investigations of the Iridium(III)-Catalyzed Aerobic Oxidation of Primary and Secondary Alcohols

被引:74
作者
Jiang, Bi [1 ]
Feng, Yuee [1 ]
Ison, Elon A. [1 ]
机构
[1] N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
关键词
D O I
10.1021/ja8049595
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The commercially available catalysts [(Cp*IrCl2)(2)] is employed with O-2 as the terminal oxidant in the presence of catalytic amounts of Et3N for the aerobic oxidation of primary and secondary alcohols. A new mechanism for the Ir-catalyzed aerobic oxidation is also presented that suggests that the transition metal maintains its +3 oxidation state throughout the entire catalytic cycle.
引用
收藏
页码:14462 / +
页数:4
相关论文
共 20 条
[1]  
ARITA S, 2008, ANGEW CHEM INT EDIT, V47, P1
[2]   Aqueous rhodium(III) hydrides and mononuclear rhodium(II) complexes [J].
Bakac, A .
DALTON TRANSACTIONS, 2006, 6 (13) :1589-1596
[3]   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
[4]   Acidic iridium hydrides: Implications for aerobic and Oppenauer oxidation of alcohols [J].
Gabrielsson, Anders ;
van Leeuwen, Piet W. N. M. ;
Kaim, Wolfgang .
CHEMICAL COMMUNICATIONS, 2006, (47) :4926-4927
[5]   Cp*Ir complexes bearing N-heterocyclic carbene ligands as effective catalysts for Oppenauer-type oxidation of alcohols [J].
Hanasaka, F ;
Fujita, KI ;
Yamaguchi, R .
ORGANOMETALLICS, 2004, 23 (07) :1490-1492
[6]   Homogeneous catalytic reduction of dioxygen using transfer hydrogenation catalysts [J].
Heiden, Zachariah M. ;
Rauchfuss, Thomas B. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (46) :14303-14310
[7]   PENTAMETHYLCYCLOPENTADIENYLRHODIUM AND -IRIDIUM HALIDES .I. SYNTHESIS AND PROPERTIES [J].
KANG, JW ;
MOSELEY, K ;
MAITLIS, PM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (22) :5970-&
[8]   Reaction of molecular oxygen with a PdII-hydride to produce a PdII-hydroperoxide:: Acid catalysis and implications for Pd-catalyzed aerobic oxidation reactions [J].
Konnick, Michael M. ;
Gandhi, Bhavesh A. ;
Guzei, Ilia A. ;
Stahl, Shannon S. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (18) :2904-2907
[9]   Dual role of (-)-sparteine in the palladium-catalyzed aerobic oxidative kinetic resolution of secondary alcohols [J].
Mueller, JA ;
Jensen, DR ;
Sigman, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (28) :8202-8203
[10]   Recent advances in transition metal catalyzed oxidation of organic substrates with molecular oxygen [J].
Punniyamurthy, T ;
Velusamy, S ;
Iqbal, J .
CHEMICAL REVIEWS, 2005, 105 (06) :2329-2363