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

被引：303

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.

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页码：57 / 68

页数：12

相关论文

共 83 条

[1] Air- and moisture-stable secondary phosphine oxides as preligands in catalysis [J].

Ackermann, Lutz .

SYNTHESIS-STUTTGART, 2006, 10 (10) :1557-1571

[2] Discovery of selective aminothiazole aurora kinase inhibitors [J].

Andersen, Carsten B. ;

Wan, Yongqin ;

Chang, Jae W. ;

Riggs, Blake ;

Lee, Christian ;

Liu, Yi ;

Sessa, Fabio ;

Villa, Fabrizio ;

Kwiatkowski, Nicholas ;

Suzuki, Melissa ;

Nallan, Laxman ;

Heald, Rebecca ;

Musacchio, Andrea ;

Gray, Nathanael S. .

ACS CHEMICAL BIOLOGY, 2008, 3 (03) :180-192

[3] Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles [J].

Anderson, Kevin W. ;

Tundel, Rachel E. ;

Ikawa, Takashi ;

Altman, Ryan A. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) :6523-6527

[4] Role of tyrosine kinase inhibitors in cancer therapy [J].

Arora, A ;

Scholar, EM .

JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2005, 315 (03) :971-979

[5] Selective palladium-catalyzed amination of the heterocyclic core of variolins [J].

Baeza, Alejandro ;

Burgos, Carolina ;

Alvarez-Builla, Julio ;

Vaquero, Juan J. .

TETRAHEDRON LETTERS, 2007, 48 (14) :2597-2601

[6] Evaluation of indazole-based compounds as a new class of potent KDR/VEGFR-2 inhibitors [J].

Bauer, David ;

Whittington, Douglas A. ;

Coxon, Angela ;

Bready, James ;

Harriman, Shawn P. ;

Patel, Vinod F. ;

Polverino, Anthony ;

Harmange, Jean-Christophe .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (17) :4844-4848

[7] First palladium-catalyzed aminations of aryl chlorides [J].

Beller, M ;

Riermeier, TH ;

Reisinger, CP ;

Herrmann, WA .

TETRAHEDRON LETTERS, 1997, 38 (12) :2073-2074

[8] A new class of easily activated palladium precatalysts for facile C-N cross-coupling reactions and the low temperature oxidative addition of aryl chlorides [J].

Biscoe, Mark R. ;

Fors, Brett P. ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (21) :6686-+

[9] Synthesis of C2-symmetric and unsymmetrically substituted 2,2′-dipyridylamines and crystal structure of a chiral 2,2′-dipyridylamine copper(II) complex [J].

Bolm, C ;

Frison, JC ;

Le Paih, J ;

Moessner, C ;

Raabe, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (23) :3767-3777

[10] Synthesis of the PhIP adduct of 2′-deoxyguanosine and its incorporation into oligomeric DNA [J].

Bonala, Radha ;

Torres, M. Cecilia ;

Iden, Charles R. ;

Johnson, Francis .

CHEMICAL RESEARCH IN TOXICOLOGY, 2006, 19 (06) :734-738

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