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
[21]   1,3-dihydro-2,1,3-benzothiadiazol-2,2-diones and 3,4-dihydro-1H-2,1,3-benzothidiazin-2,2-diones as ligands for the NOP receptor [J].
Goehring, RR ;
Whitehead, JFW ;
Brown, K ;
Islam, K ;
Xin, W ;
Zhou, XM ;
Chen, ZM ;
Valenzano, KJ ;
Miller, WS ;
Shen, S ;
Kyle, DJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (20) :5045-5050
[22]   Structural characterization and catalytic activity of the rhodium-carbene complex Rh(PPh3)2(IMes)Cl (IMes = bis(1,3-(2,4,6-trimethylphenyl)imidazol-2-ylidene) [J].
Grasa, GA ;
Moore, Z ;
Martin, KL ;
Stevens, ED ;
Nolan, SP ;
Paquet, V ;
Lebel, H .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 658 (1-2) :126-131
[23]  
Heller D, 2002, ANGEW CHEM INT EDIT, V41, P777, DOI 10.1002/1521-3773(20020301)41:5<777::AID-ANIE777>3.0.CO
[24]  
2-7
[25]   THE REACTION OF FORMALDEHYDE AND SECONDARY AMINES WITH SOME OLEFINS [J].
HENNION, GF ;
PRICE, CC ;
WOLFF, VC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (17) :4633-4636
[26]  
Herrmann W. A., 2002, ANGEW CHEM, V114, P1342, DOI [DOI 10.1002/1521-3757(20020415)114:8<1342::AID-ANGE1342>3.0.CO
[27]  
2-A, DOI 10.1016/j.ccr.2014.12.019]
[28]  
Herrmann W. A., 2006, ANGEW CHEM, V118, P3943
[29]   A carbocyclic carbene as an efficient catalyst ligand for C-C coupling reactions [J].
Herrmann, Wolfgang A. ;
Ofele, Karl ;
Schneider, Sabine K. ;
Herdtweck, Eberhardt ;
Hoffmann, Stephan D. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (23) :3859-3862
[30]   Intramolecular C-H activation involving a rhodium-imidazol-2-ylidene complex and its reaction with H2 and CO [J].
Huang, JK ;
Stevens, ED ;
Nolan, SP .
ORGANOMETALLICS, 2000, 19 (06) :1194-1197