Sonogashira reactions catalyzed by a new and efficient copper(I) catalyst incorporating N-benzyl DABCO chloride

被引：25

作者：

Hajipour, Abdol R. ^{[1
,2
]}

Mohammadsaleh, Fatemeh ^{[1
]}

机构：

[1] Isfahan Univ Technol, Dept Chem, Pharmaceut Res Lab, Esfahan 84156, Iran

[2] Univ Wisconsin, Sch Med, Dept Pharmacol, Madison, WI 53706 USA

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 24期

关键词：

Coupling reactions; Sonogashira reaction; N-Benzyl DABCO chloride; Copper(I) chloride; Catalyst; CROSS-COUPLING REACTIONS; TERMINAL ALKYNES; SUZUKI-MIYAURA; BOND FORMATION; VINYL IODIDES; ARYL HALIDES; PALLADIUM; COMPLEXES; CHEMISTRY; PERSPECTIVE;

D O I：

10.1016/j.tetlet.2014.03.120

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and effective catalytic system using [N-benzyl DABCO](+)[Cu4Cl5](-) was developed for the palladium-free Sonogashira cross-coupling reactions of phenylacetylene with a variety of aryl halides. In this homogeneous catalytic system, 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride, a quaternary ammonium salt containing a coordinating center, plays an important role and increases the efficiency of Cu(I) species during the reaction. A number of internal alkynes were produced in moderate to excellent yields, in short reaction times in DMF at 135 degrees C. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：3459 / 3462

页数：4

共 40 条

[1] Synthesis and theoretical study of a series of dipalladium(I) complexes containing the Pd2(μ-CO)2 core [J].

Baig, S ;

Richard, B ;

Serp, P ;

Mijoule, C ;

Hussein, K ;

Guihéry, N ;

Barthelat, JC ;

Kalck, P .

INORGANIC CHEMISTRY, 2006, 45 (05) :1935-1944

[2] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[3] Supported copper precatalysts for ligand-free, palladium-free Sonogashira coupling reactions [J].

Biffis, Andrea ;

Scattolin, Elena ;

Ravasio, Nicoletta ;

Zaccheria, Federica .

TETRAHEDRON LETTERS, 2007, 48 (49) :8761-8764

[4]

Cabo V., 2005, ORG LETT, V7, P617

[5]

Carril M., 2008, Angew. Chem, V120, P4940, DOI DOI 10.1002/ANGE.200801539

[6] The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].

Chinchilla, Rafael ;

Najera, Carmen .

CHEMICAL REVIEWS, 2007, 107 (03) :874-922

[7] OXIDATION OF METAL-MESO-OCTAETHYLPORPHYRINOGEN COMPLEXES LEADING TO NOVEL OXIDIZED FORMS OF PORPHYRINOGEN OTHER THAN PORPHYRINS .2. THE REDOX CHEMISTRY OF IRON(II)-MESO-OCTAETHYLPORPHYRINOGEN AND COBALT(II)-MESO-OCTAETHYLPORPHYRINOGEN COMPLEXES OCCURRING WITH THE FORMATION AND CLEAVAGE OF 2 CYCLOPROPANE UNITS [J].

DEANGELIS, S ;

SOLARI, E ;

FLORIANI, C ;

CHIESIVILLA, A ;

RIZZOLI, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :5702-5713

[8]

Doucet H., 2007, ANGEW CHEM, V119, P850, DOI DOI 10.1039/C2CC38002A

[9] Sonogashira reaction of aryl halides with terminal alkynes catalyzed by cobalt hollow nanospheres [J].

Feng, Lizhe ;

Liu, Fangxian ;

Sun, Peipei ;

Bao, Jianchun .

SYNLETT, 2008, (09) :1415-1417

[10] Carbon-Fluorine Bond Formation for the Synthesis of Aryl Fluorides [J].

Furuya, Takeru ;

Klein, Johannes E. M. N. ;

Ritter, Tobias .

SYNTHESIS-STUTTGART, 2010, (11) :1804-1821

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