Carbamoyl-substituted N-heterocyclic carbene complexes of palladium(II):: Application to Sonogashira cross-coupling reactions

被引：189

作者：

Batey, RA ^{[1
]}

Shen, M ^{[1
]}

Lough, AJ ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 09期

关键词：

D O I：

10.1021/ol017245g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] The first examples of N-carbamoyl-substituted heterocyclic carbene Pd(II) complexes are described, These thermal and hydrolytically stable complexes are readily prepared from carbamoyl imidazolium salts and efficiently promote Sonogashira cross-coupling reactions under mild conditions. Cesium carbonate is also shown to be an effective base for the coupling of aryl bromides.

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页码：1411 / 1414

页数：4

相关论文

共 41 条

[1] Highly satisfactory procedures for the Pd-catalyzed cross coupling of aryl electrophiles with in situ generated alkynylzinc derivatives [J].

Anastasia, L ;

Negishi, E .

ORGANIC LETTERS, 2001, 3 (20) :3111-3113

[2] A STABLE CRYSTALLINE CARBENE [J].

ARDUENGO, AJ ;

HARLOW, RL ;

KLINE, M .

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

[3] The quest for stable carbenes [J].

Arduengo, AJ ;

Krafczyk, R .

CHEMIE IN UNSERER ZEIT, 1998, 32 (01) :6-14

[4] Functionalized naphtho[2,3-h]quinoline-7,12-diones [J].

Barabanov, II ;

Fedenok, LG ;

Shvartsberg, MS .

RUSSIAN CHEMICAL BULLETIN, 1998, 47 (11) :2256-2261

[5] An efficient new protocol for the formation of unsymmetrical tri- and tetrasubstituted ureas [J].

Batey, RA ;

Santhakumar, V ;

Yoshina-Ishii, C ;

Taylor, SD .

TETRAHEDRON LETTERS, 1998, 39 (35) :6267-6270

[6] A new protocol for the formation of carbamates and thiocarbamates using carbamoyl imidazolium salts [J].

Batey, RA ;

Yoshina-Ishii, C ;

Taylor, SD ;

Santhakumar, V .

TETRAHEDRON LETTERS, 1999, 40 (14) :2669-2672

[7]

BATEY RA, UNPUB

[8] Silver salts as new catalyst for coupling reactions; Synthesis of epoxyenynes [J].

Bertus, P ;

Pale, P .

TETRAHEDRON LETTERS, 1996, 37 (12) :2019-2022

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

Böhm, VPW ;

Gstöttmayr, CWK ;

Weskamp, T ;

Herrmann, WA .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 595 (02) :186-190

[10] REACTIONS OF SYMMETRIC C-IMIDAZOLYLGOLD(I) LEADING TO AU(I) CARBENE COMPLEXES OR MIXED-VALENCE OR AU(III) IMIDAZOLYL DERIVATIVES - CRYSTAL-STRUCTURE OF [1-BENZYL-3-(CARBOETHOXY)IMIDAZOLIN-2-YLIDEN]CHLOROGOLD(I) [J].

BONATI, F ;

BURINI, A ;

PIETRONI, BR ;

BOVIO, B .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 408 (02) :271-280

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