Synthesis of substituted 2,2′-bipyridines from 2-bromo- or 2-chloropyridines using tetrakis(triphenylphosphine)palladium(0) as a catalyst in a modified Negishi cross-coupling reaction

被引：32

作者：

Kiehne, U. ^{[1
]}

Bunzen, J. ^{[1
]}

Staats, H. ^{[1
]}

Luetzen, A. ^{[1
]}

机构：

[1] Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany

来源：

SYNTHESIS-STUTTGART | 2007年 / 7卷 / 07期

关键词：

Negishi reaction; 2,2 '-bipyridines; cross-coupling reactions; organozinc compounds; palladium;

D O I：

10.1055/s-2007-965952

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A protocol for an efficient, modified Negishi cross-coupling strategy for substituted 2,2'-bipyridines employing tetrakis(triphenylphosphine)palladium(0) as a simple, commercially available, and relatively inexpensive catalyst for both 2-bromo- and 2-chloropyridines has been developed. Further transformations were carried out yielding some new valuable functionalized 2,2'-bipyridines.

引用

页码：1061 / 1069

页数：9

共 38 条

[1]

[Anonymous], 2002, J ORGANOMET CHEM

[2] Synthesis of conjugatively bridged bis- and tris-5-(2,2′-bipyridines):: Multitopic metal ion-binding modules for supramolecular nanoengineering [J].

Baxter, PNW .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) :1257-1272

[3] Chiral 2,2′-bipyridines, 1,10-phenanthrolines, and 2,2′:6′,2"-terpyridines:: Syntheses and applications in asymmetric homogeneous catalysis [J].

Chelucci, G ;

Thummel, RP .

CHEMICAL REVIEWS, 2002, 102 (09) :3129-3170

[4] The first general method for palladium-catalyzed Negishi cross-coupling of aryl and vinyl chlorides:: Use of commercially available Pd(P(t-BU)3)2 as a catalyst [J].

Dai, CY ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) :2719-2724

[5]

Fang YQ, 2003, SYNLETT, P852

[6] Chiral 2,2′-bipyridines:: ligands for asymmetric induction [J].

Fletcher, NC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (16) :1831-1842

[7] The isolation and purification of tris-2,2′-bipyridine complexes of ruthenium(II) containing unsymmetrical ligands [J].

Fletcher, NC ;

Nieuwenhuyzen, M ;

Rainey, S .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2001, (18) :2641-2648

[8] Shape-persistant macrocycles with terpyridine units:: Synthesis, characterization, and structure in the crystal [J].

Grave, C ;

Lentz, D ;

Schäfer, A ;

Samorì, P ;

Rabe, JP ;

Franke, P ;

Schlüter, AD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (23) :6907-6918

[9] Construction of preorganized polytopic ligands via palladium-promoted cross-coupling reactions [J].

Grosshenny, V ;

Romero, FM ;

Ziessel, R .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1491-1500

[10] TRANSFORMATIONS OF CHLOROARENES, CATALYZED BY TRANSITION-METAL COMPLEXES [J].

GRUSHIN, VV ;

ALPER, H .

CHEMICAL REVIEWS, 1994, 94 (04) :1047-1062

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