Highly reactive, general, and long-lived catalysts for coupling heteroaryl and aryl chlorides with primary nitrogen nucleophiles

被引：329

作者：

Shen, QL ^{[1
]}

Shekhar, S ^{[1
]}

Stambuli, JP ^{[1
]}

Hartwig, JF ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 09期

关键词：

amination; heterocycles; homogenenous catalysis; P ligands; palladium;

D O I：

10.1002/anie.200462629

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Resisting pathways for decomposition followed by palladium complexes of monodentate ligands is one characteristic of the highly reactive but long-lived catalyst generated from the Josiphos ligand L and palladium. It catalyzes under mild conditions the coupling of primary amines with chloropyridines and chloroarenes in high yield with low catalyst loadings (see scheme). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

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页码：1371 / 1375

页数：5

相关论文

共 46 条

[1] Mechanistic studies of the palladium-catalyzed amination of aryl halides and the oxidative addition of aryl bromides to Pd(BINAP)2 and Pd(DPPF)2:: An unusual case of zero-order kinetic behavior and product inhibition [J].

Alcazar-Roman, LM ;

Hartwig, JF ;

Rheingold, AL ;

Liable-Sands, LM ;

Guzei, IA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (19) :4618-4630

[2] Identification of the effective palladium(0) catalytic species generated in situ from mixtures of Pd(dba)(2) and bidentate phosphine ligands. Determination of their rates and mechanism in oxidative addition [J].

Amatore, C ;

Broeker, G ;

Jutand, A ;

Khalil, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (22) :5176-5185

[3]

[Anonymous], 2002, HDB ORGANOPALLADIUM

[4]

[Anonymous], 2002, J ORGANOMET CHEM

[5] Synthesis of meta-substituted aniline derivatives by nucleophilic substitution [J].

Belfield, AJ ;

Brown, GR ;

Foubister, AJ ;

Ratcliffe, PD .

TETRAHEDRON, 1999, 55 (46) :13285-13300

[6] CHELATE-ASSISTED, PD-CATALYZED EFFICIENT CARBONYLATION OF ARYL CHLORIDES [J].

BENDAVID, Y ;

PORTNOY, M ;

MILSTEIN, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (23) :8742-8744

[7] Palladium-catalyzed intermolecular coupling of aryl chlorides and sulfonamides under microwave irradiation [J].

Burton, G ;

Cao, P ;

Li, G ;

Rivero, R .

ORGANIC LETTERS, 2003, 5 (23) :4373-4376

[8]

GIAM CS, 1974, PYRIDINE ITS DERIVAT, V3, P41

[9] Amination reactions of aryl halides with nitrogen-containing reagents mediated by palladium/imidazolium salt systems [J].

Grasa, GA ;

Viciu, MS ;

Huang, JK ;

Nolan, SP .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) :7729-7737

[10] Sterically hindered chelating alkyl phosphines provide large rate accelerations in palladium-catalyzed amination of aryl iodides, bromides, and chlorides, and the first amination of aryl tosylates [J].

Hamann, BC ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (29) :7369-7370

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