N-heterocyclic NCN-pincer palladium complexes:: A source for general, highly efficient catalysts in Heck, Suzuki, and Sonogashira coupling reactions

被引：44

作者：

Churruca, F ^{[1
]}

SanMartin, R ^{[1
]}

Tellitu, I ^{[1
]}

Domínguez, E ^{[1
]}

机构：

[1] Euskal Herriko Unibersitatea, Zientia & Teknol Fak, Kim Organ Saila 2, Bilbao, Spain

来源：

SYNLETT | 2005年 / 20期

关键词：

palladacycles; catalysis; pincer complexes; cross-coupling;

D O I：

10.1055/s-2005-922754

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Readily available NCN-pincer palladium complexes comprising two pyrazole units as the source of both N-donor atoms are successfully employed as catalysts in a range of C-C bond-forming reactions. Good to excellent results are obtained in all cases regardless of the electronic nature of the substrates, along with more convenient procedures and comparatively much lower catalysts loadings in Suzuki and Sonogashira couplings. This paper presents the first report of a Sonogashira coupling reaction by means of a NCN catalyst.

引用

页码：3116 / 3120

页数：5

共 43 条

[1]

ABE T, 2004, Patent No. 2004132708

[2] SEQUENTIAL DIRECTED ORTHO METALATION BORONIC ACID CROSS-COUPLING REACTIONS - A GENERAL REGIOSPECIFIC ROUTE TO OXYGENATED DIBENZO[B,D]PYRAN-6-ONES RELATED TO ELLAGIC ACID [J].

ALO, BI ;

KANDIL, A ;

PATIL, PA ;

SHARP, MJ ;

SIDDIQUI, MA ;

SNIECKUS, V ;

JOSEPHY, PD .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :3763-3768

[3] Palladium bis(phosphinite) 'PCP'-pincer complexes and their application as catalysts in the Suzuki reaction [J].

Bedford, RB ;

Draper, SM ;

Scully, PN ;

Welch, SL .

NEW JOURNAL OF CHEMISTRY, 2000, 24 (10) :745-747

[4] Palladacycles in catalysis - a critical survey [J].

Beletskaya, IP ;

Cheprakov, AV .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (24) :4055-4082

[5] Mechanistic studies of SCS-Pd complexes used in Heck catalysis [J].

Bergbreiter, DE ;

Osburn, PL ;

Frels, JD .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (01) :172-184

[6] Functional ligands and complexes for new structures, homogeneous catalysts and nanomaterials [J].

Braunstein, P .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (24) :3953-3967

[7] A new, expeditious entry to the benzophenanthrofuran framework by a Pd-catalyzed C- and O-arylation/PIFA-mediated oxidative coupling sequence [J].

Churruca, F ;

SanMartin, R ;

Tellitu, I ;

Domínguez, E .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (12) :2481-2490

[8] APPLICATION OF A CU(I)-MEDIATED BIARYL CROSS-COUPLING REACTION TO THE SYNTHESIS OF OXYGENATED 1,1'-BINAPHTHALENES [J].

COLEMAN, RS ;

GRANT, EB .

TETRAHEDRON LETTERS, 1993, 34 (14) :2225-2228

[9]

De Meijere A., 2004, Metal-Catalyzed Cross-Coupling Reactions

[10] Aqueous-phase, palladium-catalyzed cross-coupling of aryl bromides under mild conditions, using water-soluble, sterically demanding alkylphosphines [J].

DeVasher, RB ;

Moore, LR ;

Shaughnessy, KH .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) :7919-7927

← 1 2 3 4 5 →