P[N(i-Bu)CH2CH2]3N:: A versatile ligand for the Pd-catalyzed amination of aryl chlorides

被引：84

作者：

Urgaonkar, S ^{[1
]}

Nagarajan, M ^{[1
]}

Verkade, JG ^{[1
]}

机构：

[1] Iowa State Univ Sci & Technol, Dept Chem, Ames, IA 50011 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 06期

关键词：

D O I：

10.1021/ol027450b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Graphics Palladium-catalyzed amination reactions of aryl chlorides with amines proceeded in the presence of the bicyclic triaminophosphine P[N(i-Bu)CH2CH2](3)N to afford the corresponding arylamines in good to excellent yields. Electron-poor, electron-neutral, and electron-rich aryl chlorides all participated with equal ease.

引用

页码：815 / 818

页数：4

共 32 条

[1] Mechanism of aryl chloride amination: Base-induced oxidative addition [J].

Alcazar-Roman, LM ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (51) :12905-12906

[2] Phenyl backbone-derived P,O- and P,N-ligands for palladium/ligand-catalyzed aminations of aryl bromides, iodides, and chlorides.: Syntheses and structures of (P,O)n-palladium(II)aryl(Br) complexes [J].

Bei, XH ;

Uno, T ;

Norris, J ;

Turner, HW ;

Weinberg, WH ;

Guram, AS ;

Petersen, JL .

ORGANOMETALLICS, 1999, 18 (10) :1840-1853

[3] Synthesis of bulky, electron rich hemilabile phosphines and their application in the Suzuki coupling reaction of aryl chlorides [J].

Clarke, ML ;

Cole-Hamilton, DJ ;

Woollins, JD .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2001, (19) :2721-2723

[4] P-N bond formation as a route to highly electron rich phosphine ligands [J].

Clarke, ML ;

Cole-Hamilton, DJ ;

Slawin, AMZ ;

Woollins, JD .

CHEMICAL COMMUNICATIONS, 2000, (20) :2065-2066

[5] UV PHOTO-ELECTRON SPECTROSCOPIC INVESTIGATION OF SOME POLYCYCLIC GROUP 5A COMPOUNDS AND RELATED ACYCLIC SPECIES .1. FREE AND COORDINATED AMINOPHOSPHINES AND RELATED-COMPOUNDS [J].

COWLEY, AH ;

LATTMAN, M ;

STRICKLEN, PM ;

VERKADE, JG .

INORGANIC CHEMISTRY, 1982, 21 (02) :543-549

[6]

EHRENTRAUT A, 2002, J MOL CATAL A-CHEM, V3494, P1

[7] 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

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

GRUSHIN, VV ;

ALPER, H .

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

[9]

Hartwig JF, 1998, ANGEW CHEM INT EDIT, V37, P2046, DOI 10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO

[10]

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