Cycloruthenated primary and secondary amines as efficient catalyst precursors for asymmetric transfer hydrogenation

被引:102
作者
Sortais, JB
Ritleng, V
Voelklin, A
Holuigue, A
Smail, H
Barloy, L
Sirlin, C
Verzijl, GKM
Boogers, JAF
de Vries, AHM
de Vries, JG
Pfeffer, M
机构
[1] Univ Strasbourg, CNRS, UMR 7513, Lab Synth Metallo Induites, F-67000 Strasbourg, France
[2] DSM Pharma Chem, Adv Synth Catalysis & Dev, NL-6160 MD Geleen, Netherlands
关键词
D O I
10.1021/ol047353d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ruthenacycles obtained by cyclometalation of enantiopure aromatic primary or secondary amines with [(eta(6)-benzene)RuCl2](2) or with [(eta(6)-pcymene)RuCl2](2) are efficient catalysts for asymmetric transfer hydrogenation (TOF up to 190 h(-1) at room temperature). Enantioselectivities in the transfer hydrogenation of acetophenone ranged from 38% to 89%. It is possible to prepare the catalysts in situ, which allows the use of high throughput experimentation.
引用
收藏
页码:1247 / 1250
页数:4
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共 44 条
[31]  
Noyori R, 2002, ANGEW CHEM INT EDIT, V41, P2008, DOI 10.1002/1521-3773(20020617)41:12<2008::AID-ANIE2008>3.0.CO
[32]  
2-4
[33]   Metal-ligand bifunctional catalysis: A nonclassical mechanism for asymmetric hydrogen transfer between alcohols and carbonyl compounds [J].
Noyori, R ;
Yamakawa, M ;
Hashiguchi, S .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :7931-7944
[34]   Highly active PdII cyclometallated imine catalysts for the Heck reaction [J].
Ohff, M ;
Ohff, A ;
Milstein, D .
CHEMICAL COMMUNICATIONS, 1999, (04) :357-358
[35]   Asymmetric transfer hydrogenation of C=O and C=N bonds [J].
Palmer, MJ ;
Wills, M .
TETRAHEDRON-ASYMMETRY, 1999, 10 (11) :2045-2061
[36]  
Reetz MT, 2000, ANGEW CHEM INT EDIT, V39, P3889, DOI 10.1002/1521-3773(20001103)39:21<3889::AID-ANIE3889>3.0.CO
[37]  
2-T
[38]   Ligand-free Heck reactions using low Pd-loading [J].
Reetz, MT ;
de Vries, JG .
CHEMICAL COMMUNICATIONS, 2004, (14) :1559-1563
[39]   Thermomorphic fluorous imine and thioether palladacycles as precursors for highly active Heck and Suzuki catalysts; evidence for palladium nanoparticle pathways [J].
Rocaboy, C ;
Gladysz, JA .
NEW JOURNAL OF CHEMISTRY, 2003, 27 (01) :39-49
[40]   MECHANISMS OF INTRAMOLECULAR ACTIVATION OF C-H BONDS IN TRANSITION-METAL COMPLEXES [J].
RYABOV, AD .
CHEMICAL REVIEWS, 1990, 90 (02) :403-424