Hydroaminomethylation with novel rhodium-carbene complexes: An efficient catalytic approach to pharmaceuticals

被引:72
作者
Ahmed, Moballigh [1 ]
Buch, Cathleen [1 ]
Routaboul, Lucie [1 ]
Jackstell, Ralf [1 ]
Klein, Holger [1 ]
Spannenberg, Anke [1 ]
Beller, Matthias [1 ]
机构
[1] Univ Rostock, Leibniz Inst Katalyse EV, D-18059 Rostock, Germany
关键词
amines; carbenes; carbonylation; hydroaminomethylation; pharmaceuticals; rhodium;
D O I
10.1002/chem.200601155
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Starting from [jRh(cod)Cl)21 and 1,3-dimesitylimidazole-2-ylidenes the novel [RhCl(cod)(carbene)] complexes 1-5 have been synthesized, characterized, and tested in the hydroaminomethylation of aromatic olefins. The influence of different ligands and reaction parameters on the catalytic activitywas investigated in detail applying 1,1diphenylethylene and piperidine as a model system. The scope and limitations of the novel catalysts is shown in the preparation of 16 biologically active 1-amino-3,3-diarylpropenes. In general, high chemo- and regioselectivity as well as good yields of the desired products were achieved.
引用
收藏
页码:1594 / 1601
页数:8
相关论文
共 58 条
[31]  
Jackstell R, 2002, ANGEW CHEM INT EDIT, V41, P986, DOI 10.1002/1521-3773(20020315)41:6<986::AID-ANIE986>3.0.CO
[32]  
2-M
[33]  
Jackstell R., 2002, ANGEW CHEM, V114, P1028
[34]  
Karabiyik H, 2005, Z NATURFORSCH B, V60, P837
[35]   Hydroaminomethylation of styrene with morpholine catalysed by a rhodium complex with a phosphino amino alcohol ligand [J].
Kostas, ID .
JOURNAL OF CHEMICAL RESEARCH, 1999, (10) :630-631
[36]   Contributions to the chemistry of carbenemetal chemistry [J].
Lappert, MF .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (24-25) :5467-5473
[37]   Nickel(0)/imidazolium carbene catalyst system for efficient cross-coupling of aryl bromides and chlorides with organomanganese reagents [J].
Leleu, Anne ;
Fort, Yvet ;
Schneider, Raphael .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :1086-1092
[38]   Zwitterionic rhodium complex catalyzed hydroaminomethylation of arylethylenes [J].
Lin, YS ;
El Ali, B ;
Alper, H .
TETRAHEDRON LETTERS, 2001, 42 (13) :2423-2425
[39]  
MARCHETTI M, 2003, J AM CHEM SOC, V137, P74
[40]   BEHAVIOR OF AMINE IN RHODIUM COMPLEX-TERTIARY AMINE CATALYST SYSTEM ACTIVE FOR HYDROGENATION OF ALDEHYDE UNDER OXO REACTION CONDITIONS [J].
MIZOROKI, T ;
KIOKA, M ;
SUZUKI, M ;
SAKATANI, S ;
OKUMURA, A ;
MARUYA, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (02) :577-578