Palladium Complexes of Planar Chiral Ferrocenyl Phosphine-NHC Ligands: New Catalysts for the Asymmetric Suzuki-Miyaura Reaction

被引：121

作者：

Debono, Nathalie ^{[1
,2
]}

Labande, Agnes ^{[1
,2
]}

Manoury, Eric ^{[1
,2
]}

Daran, Jean-Claude ^{[1
,2
]}

Poli, Rinaldo ^{[1
,2
,3
]}

机构：

[1] CNRS, Chim Coordinat Lab, F-31077 Toulouse, France

[2] Univ Toulouse, UPS, INPT, LCC, F-31077 Toulouse, France

[3] Inst Univ France, F-75005 Paris, France

来源：

ORGANOMETALLICS | 2010年 / 29卷 / 08期

关键词：

N-HETEROCYCLIC CARBENES; PI-ALLYL COMPLEXES; ARYL CHLORIDES; RHODIUM(I) COMPLEXES; COUPLING REACTIONS; EFFICIENT; NICKEL(II);

D O I：

10.1021/om100125k

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Air-stable neutral and cationic palladium complexes bearing chiral phosphine-N-heterocyclic carbene ligands with planar chirality only have been prepared ill moderate to good yields and characterized by NMR and X-ray diffraction studies. They are shown to catalyze the asymmetric coupling of aryl bromides with arylboronic acids in good yields and moderate enantioselectivities (up to 42% ee) with low catalyst loadings (0.1-0.5 mol %).

引用

页码：1879 / 1882

页数：4

共 41 条

[1] An N-heterocyclic carbene ligand with flexible steric bulk allows Suzuki cross-coupling of sterically hindered aryl chlorides at room temperature [J].

Altenhoff, G ;

Goddard, R ;

Lehmann, CW ;

Glorius, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3690-3693

[2] The asymmetric Suzuki coupling route to axially chiral biaryls [J].

Baudoin, O .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (20) :4223-4229

[3] C2-Symmetric Bis-Hydrazones as Ligands in the Asymmetric Suzuki-Miyaura Cross-Coupling [J].

Bermejo, Antonio ;

Ros, Abel ;

Fernandez, Rosario ;

Lassaletta, Jose M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (47) :15798-+

[4] Stable carbenes [J].

Bourissou, D ;

Guerret, O ;

Gabbaï, FP ;

Bertrand, G .

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

[5] Aminophosphine-oxazoline and phosphoramidite-oxazoline ligands and their application in asymmetric catalysis [J].

Bronger, Raymond P. J. ;

Guiry, Patrick J. .

TETRAHEDRON-ASYMMETRY, 2007, 18 (09) :1094-1102

[6] The first asymmetric Suzuki cross-coupling reaction [J].

Cammidge, AN ;

Crépy, KVL .

CHEMICAL COMMUNICATIONS, 2000, (18) :1723-1724

[7] Chiral N-heterocyclic carbenes as stereodirecting ligands in asymmetric catalysis [J].

César, V ;

Bellemin-Laponnaz, S ;

Gade, LH .

CHEMICAL SOCIETY REVIEWS, 2004, 33 (09) :619-636

[8] Phosphine- and pyridine-functionalized N-heterocyclic carbene methyl and allyl complexes of palladium. Unexpected regiospecificity of the protonation reaction of the dimethyl complexes [J].

Danopoulos, Andreas A. ;

Tsoureas, Nikolaos ;

Macgregor, Stuart A. ;

Smith, Christopher .

ORGANOMETALLICS, 2007, 26 (02) :253-263

[9] N-Heterocyclic Carbenes in Late Transition Metal Catalysis [J].

Diez-Gonzalez, Silvia ;

Marion, Nicolas ;

Nolan, Steven P. .

CHEMICAL REVIEWS, 2009, 109 (08) :3612-3676

[10] Intramolecular hydroamination with rhodium(I) and iridium(I) complexes containing a phosphine-N-heterocyclic carbene ligand [J].

Field, LD ;

Messerle, BA ;

Vuong, KQ ;

Turner, P .

ORGANOMETALLICS, 2005, 24 (17) :4241-4250

← 1 2 3 4 5 →