Ligand-Promoted Palladium-Catalyzed Aerobic Oxidation Reactions

被引:467
作者
Wang, Dian [1 ]
Weinstein, Adam B. [1 ]
White, Paul B. [1 ]
Stahl, Shannon S. [1 ]
机构
[1] Univ Wisconsin, Dept Chem, 1101 Univ Ave, Madison, WI 53706 USA
关键词
C-H OLEFINATION; HECK-TYPE REACTION; PLANAR CHIRAL FERROCENES; PD-MEDIATED ACTIVATION; WACKER-TYPE OXIDATION; AMINO-ACID LIGANDS; N BOND FORMATION; MOLECULAR-OXYGEN; KINETIC RESOLUTION; SECONDARY ALCOHOLS;
D O I
10.1021/acs.chemrev.7b00334
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Palladium-catalyzed aerobic oxidation reactions have been the focus of industrial application and extensive research efforts for nearly 60 years. A significant transition occurred in this field approximately 20 years ago, with the introduction of catalysts supported by ancillary ligands. The ligands play crucial roles in the reactions, including promotion of direct oxidation of palladium(0) by O-2, bypassing the typical requirement for Cu salts or related redox cocatalysts to facilitate oxidation of the reduced Pd catalyst; facilitation of key bond-breaking and bond-forming steps during substrate oxidation; and modulation of chemo-, regio-, or stereoselectivity of a reaction. The use of ligands has contributed to significant expansion of the scope of accessible aerobic oxidation reactions. Increased understanding of the role of ancillary ligands should promote the development of new synthetic transformations, enable improved control over the reaction selectivity, and improve catalyst activity and stability. This review surveys the different ligands that have been used to support palladium-catalyzed aerobic oxidation reactions and, where possible, describes mechanistic insights into the role played by the ancillary ligand.
引用
收藏
页码:2636 / 2679
页数:44
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