Carbenes Made Easy: Formation of Unsymmetrically Substituted N-Heterocyclic Carbene Complexes of Palladium(II), Platinum(II) and Gold(I) from Coordinated Isonitriles and their Catalytic Activity

被引：161

作者：

Hashmi, A. Stephen K. ^{[1
]}

Lothschuetz, Christian ^{[1
]}

Boehling, Constantin ^{[1
]}

Hengst, Tobias ^{[1
]}

Hubbert, Christoph ^{[1
]}

Rominger, Frank ^{[1
]}

机构：

[1] Heidelberg Univ, Inst Organ Chem, Neuenheimer Feld 270, D-69120 Heidelberg, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 17期

关键词：

amines; carbene ligands; gold; heterocycles; isonitriles; palladium; PROMOTED CYCLIZATION REACTIONS; CROSS-COUPLING REACTIONS; HINDERED ARYL CHLORIDES; X-RAY-STRUCTURE; SUZUKI-MIYAURA; ROOM-TEMPERATURE; ISOCYANIDE LIGANDS; NHC; HYDROAMINATION; ALLENES;

D O I：

10.1002/adsc.201000472

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

From palladium(II) or platinum(II) bis(isonitrile) complexes and from gold(I) isonitrile complexes, both easily available from simple precursors, the corresponding mono-N-heterocyclic carbene (NHC) complexes could be obtained selectively in good yields under very mild conditions. The reagents are simple beta-chloroammonium salts in the presence of a weak base. Unsymmetric NHC complexes are accessible. Thus over only two steps from simple metal precursors a broad variety of NHC complexes is available, the method is ideal to quickly assemble catalyst libraries. The palladium complexes are active pre-catalysts in Suzuki cross-coupling even with the additional isonitrile ligand on palladium.

引用

页码：3001 / 3012

页数：12

共 75 条

[1] Detour-free synthesis of platinum-bis-NHC chloride complexes, their structure and catalytic activity in the CH activation of methane [J].

Ahrens, Sebastian ;

Strassner, Thomas .

INORGANICA CHIMICA ACTA, 2006, 359 (15) :4789-4796

[2] ANTIVIRAL AGENTS .2. STRUCTURE-ACTIVITY RELATIONSHIPS OF COMPOUNDS RELATED TO 1-ADAMANTANAMINE [J].

ALDRICH, PE ;

HERMANN, EC ;

MEIER, WE ;

PAULSHOCK, M ;

PRICHARD, WW ;

SYNDER, JA ;

WATTS, JC .

JOURNAL OF MEDICINAL CHEMISTRY, 1971, 14 (06) :535-+

[3] 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

[4] Photochemical isomerization of N-heterocyclic carbene ruthenium hydride complexes: In situ photolysis, parahydrogen, and computational studies [J].

Ampt, Kirsten A. M. ;

Burling, Suzanne ;

Donald, Steven M. A. ;

Douglas, Susie ;

Duckett, Simon B. ;

Macgregor, Stuart A. ;

Perutz, Robin N. ;

Whittlesey, Michael K. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (23) :7452-7453

[5]

[Anonymous], 2009, ANGEW CHEM-GER EDIT, DOI DOI 10.1002/ANGE.200902942

[6] Imidazolylidenes, imidazolinylidenes and imidazolidines [J].

Arduengo, AJ ;

Krafczyk, R ;

Schmutzler, R ;

Craig, HA ;

Goerlich, JR ;

Marshall, WJ ;

Unverzagt, M .

TETRAHEDRON, 1999, 55 (51) :14523-14534

[7] MODES OF REACTION OF 2-HYDROXYALKYL ISOCYANIDES AND 3-HYDROXYALKYL ISOCYANIDES WITH METAL-COMPOUNDS - OXAZOLIDINYLIDENE AND PERHYDROOXAZINYLIDENE COMPLEXES OF PALLADIUM, PLATINUM, AND GOLD [J].

BARTEL, K ;

FEHLHAMMER, WP .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1974, 13 (09) :599-600

[8]

Bartel K., 1974, Angew. Chem, V86, P588

[9] Nitrogen Acyclic Gold(I) Carbenes: Excellent and Easily Accessible Catalysts in Reactions of 1,6-Enynes [J].

Bartolome, Camino ;

Ramiro, Zoraida ;

Garcia-Cuadrado, Domingo ;

Perez-Galan, Patricia ;

Raducan, Mihai ;

Bour, Christophe ;

Echavarren, Antonio M. ;

Espinet, Pablo .

ORGANOMETALLICS, 2010, 29 (04) :951-956

[10] Gold(I) Complexes with Hydrogen-Bond Supported Heterocyclic Carbenes as Active Catalysts in Reactions of 1,6-Enynes [J].