Cationic iridium complexes bearing imidazol-2-ylidene ligands as transfer hydrogenation catalysts

被引：206

作者：

Hillier, AC ^{[1
]}

Lee, HM ^{[1
]}

Stevens, ED ^{[1
]}

Nolan, SP ^{[1
]}

机构：

[1] Univ New Orleans, Dept Chem, New Orleans, LA 70148 USA

来源：

ORGANOMETALLICS | 2001年 / 20卷 / 20期

关键词：

D O I：

10.1021/om0103456

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthesis and characterization by X-ray crystallography of the complexes [Ir(cod)-(py)(L)]PF6 (L = IMes, 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene (2); L = IPr, 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (3); L = ICy, 1,3-bis(cyclohexyl)imidazol-2-ylidene (4)) are reported. Complexes 2-4 have been employed as catalysts for transfer hydrogenation reactions from 2-propanol to a number of unsaturated substrates and their activity compared with that of the related cationic iridium(I) species [Ir(cod)(py)(SIMes)]-PF6 (1), [Ir(cod)(py)(PCy3)]PF6 (5), and complexes formed in situ from [Ir(cod)(py)(2)]PF6 and diazabutadienes (RN=CHCH=NR, DAB-R; R = cyclohexyl, DAB-Cy; R = 2,4,6-trimethylphenyl, DAB-Mes; R = adamantyl, DAB-Ad; R = 2,4,6-trimethoxyphenyl, DAB-trimethoxyphenyl). All complexes tested were found to be active catalysts for transfer hydrogenation of ketones, with complex 4 displaying the highest activity. Complex 4 also exhibits moderate activity toward simple olefins and an aromatic nitro compound.

引用

页码：4246 / 4252

页数：7

共 75 条

[11] Asymmetric hydrogen-transfer reduction of prochiral and α,β-unsaturated ketones by iridium complexes containing optically pure aminodiphosphine ligands [J].

Bianchini, C ;

Glendenning, L ;

Zanobini, F ;

Farnetti, E ;

Graziani, M ;

Nagy, E .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1998, 132 (01) :13-19

[12] CHEMOSELECTIVE REDUCTION OF ALPHA,BETA-UNSATURATED KETONES CATALYZED BY TRANSITION-METAL COMPLEXES WITH POLYDENTATE LIGANDS [J].

BIANCHINI, C ;

PERUZZINI, M ;

FARNETTI, E ;

KASPAR, J ;

GRAZIANI, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 488 (1-2) :91-97

[13] SYNTHESIS OF THE NEW CHIRAL AMINODIPHOSPHINE LIGANDS (R)-(ALPHA-METHYLBENZYL)BIS(2-(DIPHENYLPHOSPHINO)ETHYL)AMINE AND (S)-(ALPHA-METHYLBENZYL)BIS(2-(DIPHENYLPHOSPHINO)ETHYL)AMINE AND THEIR USE IN THE ENANTIOSELECTIVE REDUCTION OF ALPHA,BETA-UNSATURATED KETONES TO ALLYLIC ALCOHOLS BY IRIDIUM CATALYSIS [J].

BIANCHINI, C ;

FARNETTI, E ;

GLENDENNING, L ;

GRAZIANI, M ;

NARDIN, G ;

PERUZZINI, M ;

ROCCHINI, E ;

ZANOBINI, F .

ORGANOMETALLICS, 1995, 14 (03) :1489-1502

[14] Iridium complexes with alpha-diimines: Catalytic hydrogen transfer from isopropanol to cyclohexanone [J].

Bikrani, M ;

Fidalgo, L ;

Garralda, MA .

POLYHEDRON, 1996, 15 (01) :83-89

[15] Catalytic hydrogen transfer activity of cationic iridium(I) complexes containing alpha-diimines [J].

Bikrani, M ;

Fidalgo, L ;

Garralda, MA ;

Ubide, C .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1997, 118 (01) :47-53

[16] Stable carbenes [J].

Bourissou, D ;

Guerret, O ;

Gabbaï, FP ;

Bertrand, G .

CHEMICAL REVIEWS, 2000, 100 (01) :39-91

[17] HYDROGEN TRANSFER .1. INTRODUCTORY SURVEY [J].

BRAUDE, EA ;

LINSTEAD, RP .

JOURNAL OF THE CHEMICAL SOCIETY, 1954, (OCT) :3544-3547

[18] Rhodium(I) and iridium(I) complexes with beta-keto phosphine or phosphino enolate ligands. Catalytic transfer dehydrogenation of cyclooctane [J].

Braunstein, P ;

Chauvin, Y ;

Nahring, J ;

DeCian, A ;

Fischer, J ;

Tiripicchio, A ;

Ugozzoli, F .

ORGANOMETALLICS, 1996, 15 (26) :5551-5567

[19] Catalytic transfer hydrogenation of ketones by the use of ruthenium complexes incorporating the new tridentate ligand, bis(2-oxazolin-2-ylmethyl)phenylphosphine [J].

Braunstein, P ;

Fryzuk, MD ;

Naud, F ;

Rettig, SJ .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1999, (04) :589-594

[20] A new class of anionic phosphinooxazoline ligands in palladium and ruthenium complexes: catalytic properties for the transfer hydrogenation of acetophenone [J].

Braunstein, P ;

Naud, F ;

Rettig, SJ .

NEW JOURNAL OF CHEMISTRY, 2001, 25 (01) :32-39

← 1 2 3 4 5 6 7 8 →