Catalytic conversions in water. Part 23: Steric effects and increased substrate scope in the palladium-neocuproine catalyzed aerobic oxidation of alcohols in aqueous solvents

被引:84
作者
ten Brink, GJ
Arends, IWCE
Hoogenraad, M
Verspui, G
Sheldon, RA
机构
[1] Delft Univ Technol, Lab Biocatalysis & Organ Chem, NL-2628 BL Delft, Netherlands
[2] Avantium Technol BV, NL-1014 BV Amsterdam, Netherlands
关键词
alcohol oxidation; dioxygen; functional groups; palladium; phenanthroline; steric effects; water;
D O I
10.1002/adsc.200303134
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The steric influence of substituents on the 2- and 9-positions of phenanthroline in the (2,9-R-2-1,10-phenanthroline)palladium(II)-catalyzed aerobic oxidation of 2-hexanol was investigated by means of high throughput experimentation. (Neocuproine)Pd-(OAc)(2) (R=CH3) was found to be a highly active catalyst for alcohol oxidation in 1:1 water/DMSO mixtures. The catalyst is unique in that it tolerates water, polar co-solvents and a wide variety of functional groups in the alcohol. Turn-over frequencies of > 1500 h(-1) were achieved and a series of alcohols was oxidised with 0.1 to 0.5 mol % of catalyst.
引用
收藏
页码:1341 / 1352
页数:12
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