Synthesis and catalytic activity of novel xylyl-linked benzimidazolium salts

被引：27

作者：

Demir, Serpil ^{[1
]}

Ozdemir, Ismail ^{[1
]}

Cetinkaya, Bekir ^{[2
]}

机构：

[1] Inonu Univ, Fac Sci & Art, Dept Chem, TR-44280 Malatya, Turkey

[2] Ege Univ, Fac Sci, Dept Chem, TR-35100 Bornova, Turkey

来源：

APPLIED ORGANOMETALLIC CHEMISTRY | 2009年 / 23卷 / 12期

关键词：

bisbenzimidazolium chlorides; carbene; palladium catalysis; Heck coupling; CROSS-COUPLING REACTIONS; N-HETEROCYCLIC CARBENES; HECK REACTION; ARYL BROMIDES; HOMOGENEOUS CATALYSTS; CONVENIENT CATALYST; SUZUKI REACTION; MIZOROKI-HECK; PALLADIUM; COMPLEXES;

D O I：

10.1002/aoc.1558

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The reaction of 1-alkylbenzimidazole derivatives with o-/p-di(chloromethyl) benzene results in the formation of the new o-/p-xylyl-linked bis(benzimidazolium) salts, 1 and 2, respectively. The salts were characterized by NMR spectroscopy and elemental analysis. The in situ prepared complexes derived from Pd(OAc)(2)-1 and 2 exhibit catalytic activity (61-98%), to give the Heck coupling products of aryl bromides and styrene. Copyright (C) 2009 John Wiley & Sons, Ltd.

引用

页码：520 / 523

页数：4

共 38 条

[1] Extension of the alkane bridge in BisNHC-Palladium-Chloride complexes. Synthesis, structure, and catalytic activity [J].

Ahrens, Sebastian ;

Zeller, Alexander ;

Taige, Maria ;

Strassner, Thomas .

ORGANOMETALLICS, 2006, 25 (22) :5409-5415

[2] On C-C coupling by carbene-stabilized palladium catalysts: A density functional study of the Heck reaction [J].

Albert, K ;

Gisdakis, P ;

Rosch, N .

ORGANOMETALLICS, 1998, 17 (08) :1608-1616

[3] A STABLE CRYSTALLINE CARBENE [J].

ARDUENGO, AJ ;

HARLOW, RL ;

KLINE, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363

[4] Suzuki-Miyaura cross-coupling of aryl and alkyl halides using palladium/imidazolium salt protocols [J].

Arentsen, K ;

Caddick, S ;

Geoffrey, F ;

Cloke, N ;

Herring, AP ;

Hitchcock, PB .

TETRAHEDRON LETTERS, 2004, 45 (17) :3511-3515

[5] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

[6] Stable carbenes [J].

Bourissou, D ;

Guerret, O ;

Gabbaï, FP ;

Bertrand, G .

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

[7] A novel tridentate NHC-Pd(II) complex and its application in the Suzuki and Heck-type cross-coupling reactions [J].

Chen, Tao ;

Gao, Jun ;

Shi, Min .

TETRAHEDRON, 2006, 62 (26) :6289-6294

[8]

Collman J.P., 1987, PRINCIPLES APPL ORGA

[9] Mono-, Bi- and Tridentate N-Heterocyclic Carbene Ligands for the Preparation of Transition-Metal-Based Homogeneous Catalysts [J].

Corberan, Rosa ;

Mas-Marza, Elena ;

Peris, Eduardo .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2009, (13) :1700-1716

[10] Use of bis(benzimidazolium) -: palladium system as a convenient catalyst for Heck and Suzuki coupling reactions of aryl bromides and chlorides [J].

Demir, S ;

Özdemir, I ;

Çetinkaya, B .

APPLIED ORGANOMETALLIC CHEMISTRY, 2006, 20 (04) :254-259

← 1 2 3 4 →