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

页码：1345 / 1350

页数：6

共 14 条

[1] Trifluoromethyl-substituted indenyl rhodium and iridium complexes are highly selective catalysts for directed hydroboration reactions
Brinkman, JA
Nguyen, TT
Sowa, JR
[J]. 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
Calhorda, MJ
Veiros, LF
[J]. COORDINATION CHEMISTRY REVIEWS, 1999, 185-6 : 37 - 51
[6] Facile and reversible O-H and C-H activation by a chiral Iridium(I) complex
Dorta, R
Togni, A
[J]. ORGANOMETALLICS, 1998, 17 (16) : 3423 - 3428
[7] The [IrCl(diphosphine)](2)/fluoride system. Developing catalytic asymmetric olefin hydroamination
Dorta, R
Egli, P
Zurcher, F
Togni, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) : 10857 - 10858
[8] Catalytic addition of C-H bonds to multiple bonds
Murai, S
Chatani, N
Kakiuchi, F
[J]. 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
Namyslo, JC
Kaufmann, DE
[J]. CHEMISCHE BERICHTE-RECUEIL, 1997, 130 (09): : 1327 - 1331
[10] RING-SLIPPAGE CHEMISTRY OF TRANSITION-METAL CYCLOPENTADIENYL AND INDENYL COMPLEXES
OCONNOR, JM
CASEY, CP
[J]. CHEMICAL REVIEWS, 1987, 87 (02) : 307 - 318

← 1 2 →