Palladium-Catalyzed Monoarylation of Aryl Amine with Aryl Tosylates

被引：26

作者：

Xie, Xiaomin ^{[1
]}

Ni, Gang ^{[2
]}

Ma, Fangfang ^{[1
]}

Ding, Lina ^{[3
]}

Xu, Sheng ^{[2
]}

Zhang, Zhaoguo ^{[1
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China

[2] E China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai 200237, Peoples R China

[3] Heilongjiang Univ, Sch Chem Chem Engn & Mat, Harbin 150000, Peoples R China

来源：

SYNLETT | 2011年 / 07期

基金：

中国国家自然科学基金;

关键词：

palladium; ligand; monoarylation; aryl tosylate; aryl amine; CROSS-COUPLING REACTIONS; OXIDATIVE ADDITION; C-N; SUZUKI-MIYAURA; AMINATION; SULFONATES; CHLORIDES; BROMIDES; HALIDES; PD(BINAP)(2);

D O I：

10.1055/s-0030-1259728

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The bulky and electron-rich MOP-type ligand was efficient for the Pd-catalyzed amination of aryl tosylates. The in situ generated Pd(0) was a more efficient catalyst precursor than Pd(dba)(2). In the presence of Pd(OAc)(2), PhB(OH)(2), and a hindered and electron-rich MOP-type ligand, a variety of primary aryl amines reacted with various aryl tosylates to form the corresponding secondary aryl amines in high yields with high selectivity. Furthermore, the catalyst system was also efficient for the arylation of indoles and hydrazones with aryl tosylates.

引用

页码：955 / 958

页数：4

共 39 条

[1] Palladium-Catalyzed Direct Arylations of Heteroarenes with Tosylates and Mesylates [J].

Ackermann, Lutz ;

Althammer, Andreas ;

Fenner, Sabine .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) :201-204

[2] 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

[3] Mechanistic studies on oxidative addition of aryl halides and triflates to Pd(BINAP)2 and structural characterization of the product from aryl triflate addition in the presence of amine [J].

Alcazar-Roman, LM ;

Hartwig, JF .

ORGANOMETALLICS, 2002, 21 (03) :491-502

[4] Recent synthetic advances in the nucleophilic amination of benzenes [J].

Belfield, AJ ;

Brown, GR ;

Foubister, AJ .

TETRAHEDRON, 1999, 55 (38) :11399-11428

[5] A Versatile Catalyst System for Suzuki-Miyaura Cross-Coupling Reactions of C(sp2)-Tosylates and Mesylates [J].

Bhayana, Brijesh ;

Fors, Brett P. ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2009, 11 (17) :3954-3957

[6] Industrial-scale palladium-catalyzed coupling of aryl halides and amines - A personal account [J].

Buchwald, SL ;

Mauger, C ;

Mignani, G ;

Scholz, U .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (1-2) :23-39

[7] Palladium-Catalyzed Sonogashira Coupling of Aryl Mesylates and Tosylates [J].

Choy, Pui Ying ;

Chow, Wing Kin ;

So, Chau Ming ;

Lau, Chak Po ;

Kwong, Fuk Yee .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (33) :9982-9985

[8] Monoligated palladium species as catalysts in cross-coupling reactions [J].

Christmann, U ;

Vilar, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (03) :366-374

[9] Pd-Catalyzed Cross-Coupling Reactions of Amides and Aryl Mesylates [J].

Dooleweerdt, Karin ;

Fors, Brett P. ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2010, 12 (10) :2350-2353

[10] Exploiting noninnocent (E,E)-dibenzylideneacetone (dba) effects in palladium(0)-mediated cross-coupling reactions:: Modulation of the electronic properties of dba affects catalyst activity and stability in ligand and ligand-free reaction systems [J].

Fairlamb, Ian J. S. ;

Kapdi, Anant R. ;

Lee, Adam F. ;

McGlacken, Gerard P. ;

Weissburger, Felix ;

de Vries, Andre H. M. ;

Schmieder-van de Vondervoort, Lizette .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (34) :8750-8761

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