A palladium complex containing a new C2-symmetric bidentate non-racemic oxalamidine ligand:: synthesis and catalytic properties

被引:21
作者
Dupont, J
Ebeling, G
Delgado, MR
Consorti, CS
Burrow, R
Farrar, DH
Lough, AJ
机构
[1] Univ Fed Rio Grande Sul, Lab Mol Catalysis, Inst Chem, BR-91501970 Porto Alegre, RS, Brazil
[2] Univ Fed Santa Maria, Dept Quim, BR-97105900 Santa Maria, RS, Brazil
[3] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
关键词
palladium; catalysis; amidines; hydro-arylation; asymmetric;
D O I
10.1016/S1387-7003(01)00249-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Non-racemic (S, S, S, S)-(-)-2,2-bis-(4,5-diphenyl-1, 3-imidazoline) 1 has been prepared in good yields from the reaction of (S, S)(-)1,2-diphenylethylenediamine with diethyl oxalimidate. The reaction of 1 with sodium tetrachloropalladate yields [PdCl2(1)] complex 2, whose structure has been ascertained by means of X-ray diffraction analysis. Complex 2 catalyzes the hydro-arylation of norbornene in good catalytic activity but with poor enantioselectivity. (C) 2001 Elsevier Science BN. All rights reserved.
引用
收藏
页码:471 / 474
页数:4
相关论文
共 19 条
[1]   New highly active chiral phosphapalladacycle catalysts. First isolation and characterization of a Pd(IV) intermediate [J].
Brunel, JM ;
Hirlemann, MH ;
Heumann, A ;
Buono, G .
CHEMICAL COMMUNICATIONS, 2000, (19) :1869-1870
[2]  
Brunner H, 1993, HDB ENANTIOSELECTIVE, V1
[3]   Preparation and characterization of the disjoint diradical 4,4'-bis(1,2,3,5-dithiadiazolyl) [S2N2C-CN2S2] and its iodine charge transfer salt [S2N2C-CN2S2] [J].
Bryan, CD ;
Cordes, AW ;
Goddard, JD ;
Haddon, RC ;
Hicks, RG ;
MacKinnon, CD ;
Mawhinney, RC ;
Oakley, RT ;
Palstra, TTM ;
Perel, AS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (02) :330-338
[4]   A simplified synthesis of (+/-)-1,2-diphenyl-1,2-diaminoethane (1) from benzaldehyde and ammonia. Revision of the structures of the long-known intermediates ''hydrobenzamide'' and ''amarine'' [J].
Corey, EJ ;
Kuhnle, FNM .
TETRAHEDRON LETTERS, 1997, 38 (50) :8631-8634
[5]   Cyclopropanation with diazomethane and bis(oxazoline)palladium(II) complexes [J].
Denmark, SE ;
Stavenger, RA ;
Faucher, AM ;
Edwards, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (10) :3375-3389
[6]   Nitrogen-containing ligands for asymmetric homogeneous and heterogeneous catalysis [J].
Fache, F ;
Schulz, E ;
Tommasino, ML ;
Lemaire, M .
CHEMICAL REVIEWS, 2000, 100 (06) :2159-2231
[8]   C2-symmetric chiral bis(oxazoline)-metal complexes in catalytic asymmetric synthesis [J].
Ghosh, AK ;
Packiarajan, M ;
Cappiello, J .
TETRAHEDRON-ASYMMETRY, 1998, 9 (01) :1-45
[9]  
HELMCHEN G, 1991, SYNLETT, P257
[10]  
Jacobsen E. N., 1999, COMPREHENSIVE ASYMME, V1- 3