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
来源：
ORGANIC LETTERS | 2005年 / 7卷 / 07期
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.
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页码：1247 / 1250
页数：4
相关论文
共 44 条
[1]   CARBON-CARBON AND CARBON-NITROGEN BOND FORMATION MEDIATED BY RUTHENIUM(II) COMPLEXES - SYNTHESIS OF (1H)-ISOQUINOLINIUM DERIVATIVES [J].
ABBENHUIS, HCL ;
PFEFFER, M ;
SUTTER, JP ;
DECIAN, A ;
FISCHER, J ;
JI, HL ;
NELSON, JH .
ORGANOMETALLICS, 1993, 12 (11) :4464-4472
[2]   Chiral platinum and palladium complexes containing functionalized C2-symmetric bisaminoaryl 'Pincer' ligands [J].
Albrecht, M ;
Kocks, BM ;
Spek, AL ;
van Koten, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 624 (1-2) :271-286
[3]   The first Ru(η3-PCP) complexes of the electron-rich pincer ligand 1,3-bis((dicyclohexylphosphino)methyl)benzene:: Structure and mechanism in transfer hydrogenation catalysis [J].
Amoroso, D ;
Jabri, A ;
Yap, GPA ;
Gusev, DG ;
dos Santos, EN ;
Fogg, DE .
ORGANOMETALLICS, 2004, 23 (17) :4047-4054
[4]  
ARCHIBALD B, 2002, HDB COMBINATORIAL CH, V2, P885
[5]   REACTION OF SILVER ION WITH [ML2X2] (L = AMINE OR PHOSPHINE M = PD OR PT X = I, CL, OR SCN) LEADING TO ORTHOMETALLATION AND CATALYTIC ACTIVITY - X-RAY STRUCTURE OF AB-(2-AMINOMETHYL)PHENYL-C-CARBONYL-D-IODOPLATINUM(II) [J].
AVSHU, A ;
OSULLIVAN, RD ;
PARKINS, AW ;
ALCOCK, NW ;
COUNTRYMAN, RM .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1983, (08) :1619-1624
[6]   Cyclometalated ruthenium(II) complexes as highly active transfer hydrogenation catalysts [J].
Baratta, W ;
Da Ros, P ;
Del Zotto, A ;
Sechi, A ;
Zangrando, E ;
Rigo, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (27) :3584-3588
[7]   Palladacyclic catalysts in C-C and C-heteroatom bond-forming reactions [J].
Bedford, RB .
CHEMICAL COMMUNICATIONS, 2003, (15) :1787-1796
[8]   Palladacycles in catalysis - a critical survey [J].
Beletskaya, IP ;
Cheprakov, AV .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (24) :4055-4082
[9]   Tridentate SCS palladium(II) complexes: New, highly stable, recyclable catalysts for the heck reaction [J].
Bergbreiter, DE ;
Osburn, PL ;
Liu, YS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) :9531-9538
[10]  
Carmona D, 2002, EUR J INORG CHEM, P2239
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