Iridium(I)-catalyzed asymmetric intermolecular hydroarylation of norbornene with benzamide

被引:69
作者
Aufdenblatten, R [1 ]
Diezi, S [1 ]
Togni, A [1 ]
机构
[1] ETH Zentrum, Swiss Fed Inst Technol, Inorgan Chem Lab, CH-8092 Zurich, Switzerland
来源
MONATSHEFTE FUR CHEMIE | 2000年 / 131卷 / 12期
关键词
iridium; asymmetric catalysis; hydroarylation; hydroamination; norbornene;
D O I
10.1007/s007060070014
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Starting from the dinuclear chloro-bridged Ir(I) complexes [IrCl(PP)](2) (PP=(R)-(6,6'-dimethylbiphenyl-2,2'-diyl)- 1, 1'-bis-(diphenylphosphine),and (R)-1-((S)-2-(diphenlyphosphino-ferrocenyl))-ethyldicyclohexyl-phosphine),a new class of cyclopentadienyl Ir(I) complexes containing a chiral bisphosphine ([IrCp(PP)]) was prepared and characterized. These new complexes are suited precatalysts for the direct hydroarylation of norbornene with benzamide. 2-(exo-Norbornyl)-benzamide is formed with an enantiomeric excess of up to 94% by the use of 1 mol% iridium, albeit in low yield.
引用
收藏
页码:1345 / 1350
页数:6
相关论文
共 14 条
[1]   Trifluoromethyl-substituted indenyl rhodium and iridium complexes are highly selective catalysts for directed hydroboration reactions [J].
Brinkman, JA ;
Nguyen, TT ;
Sowa, JR .
ORGANIC LETTERS, 2000, 2 (07) :981-983
[2]  
Brunel JM, 2000, ANGEW CHEM INT EDIT, V39, P1946, DOI 10.1002/1521-3773(20000602)39:11<1946::AID-ANIE1946>3.3.CO
[3]  
2-9
[4]  
BRUNEL JM, 2000, ANGEW CHEM, V122, P2022
[5]   Ring slippage in indenyl complexes: structure and bonding [J].
Calhorda, MJ ;
Veiros, LF .
COORDINATION CHEMISTRY REVIEWS, 1999, 185-6 :37-51
[6]   Facile and reversible O-H and C-H activation by a chiral Iridium(I) complex [J].
Dorta, R ;
Togni, A .
ORGANOMETALLICS, 1998, 17 (16) :3423-3428
[7]   The [IrCl(diphosphine)](2)/fluoride system. Developing catalytic asymmetric olefin hydroamination [J].
Dorta, R ;
Egli, P ;
Zurcher, F ;
Togni, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) :10857-10858
[8]   Catalytic addition of C-H bonds to multiple bonds [J].
Murai, S ;
Chatani, N ;
Kakiuchi, F .
PURE AND APPLIED CHEMISTRY, 1997, 69 (03) :589-594
[9]   Palladium-catalyzed reactions .1. Palladium-catalyzed enantioselective hydrophenylation and hydrohetarylation of bicyclo[2.2.1]hept-2-ene: Influence of the chiral ligand, the leaving group, and the solvent [J].
Namyslo, JC ;
Kaufmann, DE .
CHEMISCHE BERICHTE-RECUEIL, 1997, 130 (09) :1327-1331
[10]   RING-SLIPPAGE CHEMISTRY OF TRANSITION-METAL CYCLOPENTADIENYL AND INDENYL COMPLEXES [J].
OCONNOR, JM ;
CASEY, CP .
CHEMICAL REVIEWS, 1987, 87 (02) :307-318