Palladium-catalyzed coupling of functionalized primary and secondary amines with aryl and heteroaryl halides: two ligands suffice in most cases

被引：307

作者：

Maiti, Debabrata ^{[1
]}

Fors, Brett P. ^{[1
]}

Henderson, Jaclyn L. ^{[1
]}

Nakamura, Yoshinori ^{[1
]}

Buchwald, Stephen L. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

CHEMICAL SCIENCE | 2011年 / 2卷 / 01期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

N-HETEROCYCLIC CARBENES; LONG-LIVED CATALYSTS; C-N; BUCHWALD-HARTWIG; AMINATION REACTIONS; SUZUKI-MIYAURA; BOND FORMATION; ELECTRON-RICH; EFFICIENT; IMATINIB;

D O I：

10.1039/c0sc00330a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report our studies on the use of two catalyst systems, based on the ligands BrettPhos and RuPhos, which provide the widest scope for Pd-catalyzed C-N cross-coupling reactions to date. Often low catalyst loadings and short reaction times can be used with functionalized aryl and heteroaryl coupling partners. The reactions are highly robust and can be set up and performed without the use of a glovebox. These catalysts should find wide application in the synthesis of complex molecules including pharmaceuticals, natural products and functional materials.

引用

收藏

页码：57 / 68

页数：12

相关论文

共 83 条

[61] New ligands for a general palladium-catalyzed amination of aryl and heteroaryl chlorides [J].

Rataboul, F ;

Zapf, A ;

Jackstell, R ;

Harkal, S ;

Riermeier, T ;

Monsees, A ;

Dingerdissen, U ;

Beller, M .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (12) :2983-2990

[62] An improved synthesis of N-aryl and N-heteroaryl substituted homopiperazines-from conventional thermal conditions to scaling-up using microwave heating [J].

Schoen, Uwe ;

Messinger, Josef ;

Buckendahl, M. ;

Prabhu, M. S. ;

Konda, A. .

TETRAHEDRON, 2009, 65 (39) :8125-8131

[63] Synthesis of C8-adenosine adducts of arylamines using palladium catalysis [J].

Schoffers, E ;

Olsen, PD ;

Means, JC .

ORGANIC LETTERS, 2001, 3 (26) :4221-4223

[64] Palladium-catalyzed couplings of heteroaryl amines with aryl halides using sodium phenolate as the stoichiometric base [J].

Schulte, James P., II ;

Tweedie, Scott R. .

SYNLETT, 2007, (15) :2331-2336

[65] [(CyPF-tBu)PdCl2]:: An air-stable, one-component, highly efficient catalyst for amination of heteroaryl and aryl halides [J].

Shen, Qilong ;

Hartwig, John F. .

ORGANIC LETTERS, 2008, 10 (18) :4109-4112

[66] Highly reactive, general and long-lived catalysts for palladium-catalyzed amination of heteroaryl and aryl chlorides, bromides, and iodides: Scope and structure-activity relationships [J].

Shen, Qilong ;

Ogata, Tokutaro ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (20) :6586-6596

[67] Lewis acid acceleration of C-N bond-forming reductive elimination from heteroarylpalladium complexes and catalytic amidation of heteroaryl bromides [J].

Shen, Qilong ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (25) :7734-+

[68] Highly reactive, general, and long-lived catalysts for coupling heteroaryl and aryl chlorides with primary nitrogen nucleophiles [J].

Shen, QL ;

Shekhar, S ;

Stambuli, JP ;

Hartwig, JF .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (09) :1371-1375

[69] Switching the Chemoselectivity in the Amination of 4-Chloroquinazolines with Aminopyrazoles [J].

Shen, Zhenlu ;

Hong, Yiming ;

He, Xiaofei ;

Mo, Weimin ;

Hu, Baoxiang ;

Sun, Nan ;

Hu, Xinquan .

ORGANIC LETTERS, 2010, 12 (03) :552-555

[70] Biaryl phosphane ligands in palladium-catalyzed amination [J].

Surry, David S. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (34) :6338-6361

← 1 2 3 4 5 6 7 8 9 →