Expanding Pd-catalyzed C-N bond-forming processes: The first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions

被引:725
作者
Huang, XH [1 ]
Anderson, KW [1 ]
Zim, D [1 ]
Jiang, L [1 ]
Klapars, A [1 ]
Buchwald, SL [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1021/ja035483w
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first general method for the Pd-catalyzed amination of aryl tosylates and benzenesulfonates was developed utilizing ligand 1, which belongs to a new generation of biaryl monophosphine ligands. In addition, the new catalyst system for the first time enables amidation of aryl arenesulfonates and aqueous amination protocols that do not necessitate the use of cosolvents. The substrate scope has been significantly expanded to include aryl halides containing primary amides and free carboxylic acid groups. In the case of multifunctional substrates, the Pd-catalyzed amination can provide selectivity that is complementary to the Cu-catalyzed C-N bond-forming processes. Copyright © 2003 American Chemical Society.
引用
收藏
页码:6653 / 6655
页数:3
相关论文
共 23 条
  • [1] Palladium-catalyzed enantioselective oxidation of alcohols:: A dramatic rate acceleration by Cs2CO3/t-BuOH
    Bagdanoff, JT
    Ferreira, EM
    Stoltz, BM
    [J]. ORGANIC LETTERS, 2003, 5 (06) : 835 - 837
  • [2] High-activity catalysts for Suzuki coupling and amination reactions with deactivated aryl chloride substrates: Importance of the palladium source
    Bedford, RB
    Cazin, CSJ
    Coles, SJ
    Gelbrich, T
    Horton, PN
    Hursthouse, MB
    Light, ME
    [J]. ORGANOMETALLICS, 2003, 22 (05) : 987 - 999
  • [3] Bolm C, 2000, SYNTHESIS-STUTTGART, P911
  • [4] 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
  • [5] Sterically hindered chelating alkyl phosphines provide large rate accelerations in palladium-catalyzed amination of aryl iodides, bromides, and chlorides, and the first amination of aryl tosylates
    Hamann, BC
    Hartwig, JF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (29) : 7369 - 7370
  • [6] Improved functional group compatibility in the palladium-catalyzed synthesis of aryl amines
    Harris, MC
    Huang, XH
    Buchwald, SL
    [J]. ORGANIC LETTERS, 2002, 4 (17) : 2885 - 2888
  • [7] Hartwig, 2002, Handbook of Organopalladium Chemistry for Organic Synthesis, P1051, DOI [DOI 10.1002/0471212466.CH42, 10.1002/0471212466.ch42]
  • [8] HARTWIG JF, 2001, Patent No. 6235938
  • [9] Kaye S, 2001, ADV SYNTH CATAL, V343, P789, DOI 10.1002/1615-4169(20011231)343:8<789::AID-ADSC789>3.0.CO
  • [10] 2-A