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
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
收藏
页码:815 / 818
页数:4
相关论文
共 32 条
  • [1] Mechanism of aryl chloride amination: Base-induced oxidative addition
    Alcazar-Roman, LM
    Hartwig, JF
    [J]. 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
    Bei, XH
    Uno, T
    Norris, J
    Turner, HW
    Weinberg, WH
    Guram, AS
    Petersen, JL
    [J]. 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
    Clarke, ML
    Cole-Hamilton, DJ
    Woollins, JD
    [J]. 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
    Clarke, ML
    Cole-Hamilton, DJ
    Slawin, AMZ
    Woollins, JD
    [J]. 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
    COWLEY, AH
    LATTMAN, M
    STRICKLEN, PM
    VERKADE, JG
    [J]. 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
    Grasa, GA
    Viciu, MS
    Huang, JK
    Nolan, SP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) : 7729 - 7737
  • [8] TRANSFORMATIONS OF CHLOROARENES, CATALYZED BY TRANSITION-METAL COMPLEXES
    GRUSHIN, VV
    ALPER, H
    [J]. 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] 2-L