N-heterocyclic carbenes Part 26.: N-heterocyclic carbene complexes of palladium(0):: synthesis and application in the Suzuki cross-coupling reaction

被引：312

作者：

Böhm, VPW ^{[1
]}

Gstöttmayr, CWK ^{[1
]}

Weskamp, T ^{[1
]}

Herrmann, WA ^{[1
]}

机构：

[1] Tech Univ Munich, Inst Anorgan Chem, D-85747 Garching, Germany

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2000年 / 595卷 / 02期

关键词：

palladium; N-heterocyclic carbenes; cross coupling; carbon-carbon bond formation; Suzuki reaction;

D O I：

10.1016/S0022-328X(99)00590-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Palladium(0) complexes of N-heterocyclic carbenes (NHC) are easily obtained starting from the free carbene and bis(tri-ortho- tolylphosphine)palladium(0) by ligand exchange. The complexes [(R)N(H)C=C(H)N(R)C](2)Pd of various 1,3-disubstituted imidazolin-2-ylidenes have been prepared by this method (R = mesityl, t-Bu, i-Pr, cyclohexyl). The activities of these complexes as catalysts for the activation of chloroarenes in the Suzuki cross-coupling reaction were evaluated. Turnover frequencies up to 552 (mol product x mol Pd-1 x h(-1)] were achieved without specific optimization of the system. (C) 2000 Elsevier Science S.A. All rights reserved.

引用

页码：186 / 190

页数：5

共 45 条

[1]

[Anonymous], ANGEW CHEM

[2]

[Anonymous], ANGEW CHEM

[3]

[Anonymous], ANGEW CHEM

[4] Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers [J].

Aranyos, A ;

Old, DW ;

Kiyomori, A ;

Wolfe, JP ;

Sadighi, JP ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) :4369-4378

[5] LOW-COORDINATE CARBENE COMPLEXES OF NICKEL(0) AND PLATINUM(0) [J].

ARDUENGO, AJ ;

GAMPER, SF ;

CALABRESE, JC ;

DAVIDSON, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (10) :4391-4394

[6] Metal vapor synthesis as a straightforward route to group 10 homoleptic carbene complexes [J].

Arnold, PL ;

Cloke, FGN ;

Geldbach, T ;

Hitchcock, PB .

ORGANOMETALLICS, 1999, 18 (16) :3228-3233

[7] General and efficient palladium-catalyzed aminations of aryl chlorides [J].

Bei, XH ;

Guram, AS ;

Turner, HW ;

Weinberg, WH .

TETRAHEDRON LETTERS, 1999, 40 (07) :1237-1240

[8] Room-temperature palladium-catalyzed amination of aryl bromides and chlorides and extended scope of aromatic C-N bond formation with a commercial ligand [J].

Hartwig, JF ;

Kawatsura, M ;

Hauck, SI ;

Shaughnessy, KH ;

Alcazar-Roman, LM .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5575-5580

[9]

Herrmann W., 1997, Angew. Chem. Int. Ed. Engl, V109, P2256

[10]

Herrmann W. A., 1995, ANGEW CHEM, V107, P2602

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