Palladium-neocuproine catalyzed aerobic oxidation of alcohols in aqueous solvents

被引:56
作者
Arends, IWCE [1 ]
ten Brink, GJ [1 ]
Sheldon, RA [1 ]
机构
[1] Delft Univ Technol, Lab Biocatalysis & Organ Chem, NL-2628 BL Delft, Netherlands
关键词
palladium; phenanthroline; alcohol oxidation; dioxygen; water;
D O I
10.1016/j.molcata.2006.02.001
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
An overview is presented on the performance of Pd-complexes with phenanthroline-type ligands that are highly active catalysts for alcohol oxidation in water as well as in water/polar co-solvent mixtures. The mechanistic details of this intriguingly active and stable Pd-species are summarized. The (neocuproine)Pd(OAc)(2) catalyst is unique in that it tolerates water, polar co-solvents and a wide variety of functional groups in the alcohol. Turnover frequencies of > 1500 h(-1) were achieved in the latter case and a series of alcohols was oxidized with 0.1-0.5 mol% of catalyst. (c) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码:246 / 254
页数:9
相关论文
共 81 条
[11]  
CAINELLI G, 1984, CHROMIUM OXIDANTS OR
[12]  
Chaudhuri P, 1999, ANGEW CHEM INT EDIT, V38, P1095, DOI 10.1002/(SICI)1521-3773(19990419)38:8<1095::AID-ANIE1095>3.0.CO
[13]  
2-I
[14]  
deNooy AEJ, 1996, SYNTHESIS-STUTTGART, P1153
[15]   Efficient and selective aerobic oxidation of alcohols into aldehydes and ketones using ruthenium/TEMPO as the catalytic system [J].
Dijksman, A ;
Marino-González, A ;
Payeras, AMI ;
Arends, IWCE ;
Sheldon, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (28) :6826-6833
[16]   Selective hydrolysis of the unactivated peptide bond in N-acetylated L-histidylglycine catalyzed by various palladium(II) complexes: dependence of the hydrolysis rate on the steric bulk of the catalyst [J].
Djuran, MI ;
Milinkovic, SU .
POLYHEDRON, 2000, 19 (08) :959-963
[17]   An oxidation of alcohols by oxygen with the enzyme laccase and mediation by TEMPO [J].
Fabbrini, M ;
Galli, C ;
Gentili, P ;
Macchitella, D .
TETRAHEDRON LETTERS, 2001, 42 (43) :7551-7553
[18]   Comparing the catalytic efficiency of some mediators of laccase [J].
Fabbrini, M ;
Galli, C ;
Gentili, P .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2002, 16 (5-6) :231-240
[19]   Bowl-shaped and highly inert bis(μ-hydroxo)-platinum(II) dimer [J].
Fekl, U ;
van Eldik, R ;
Richardson, C ;
Robinson, WT .
INORGANIC CHEMISTRY, 2001, 40 (13) :3247-+
[20]   The palladiuim-catalyzed oxidative kinetic resolution of secondary alcohols with molecular oxygen [J].
Ferreira, EM ;
Stoltz, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (31) :7725-7726