Synthesis of substituted oxindoles from α-chloroacetanilides via palladium-catalyzed C-H functionalization

被引:334
作者
Hennessy, EJ [1 ]
Buchwald, SL [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1021/ja037546g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel method for the synthesis of oxindoles is described. In the presence of catalytic palladium acetate and 2-(di-tert-butylphosphino)biphenyl, α-chloroacetanilides are converted to oxindoles in good to excellent yields with high functional group compatibility using triethylamine as a stoichiometric base. The cyclization is highly regioselective, obviating the need for prefunctionalized arenes. Plausible mechanistic pathways for the reaction are discussed. Copyright © 2003 American Chemical Society.
引用
收藏
页码:12084 / 12085
页数:2
相关论文
共 35 条
  • [1] Bonding modes in palladium(II) enolates:: Consequences for dynamic behavior and reactivity
    Albéniz, AC
    Catalina, NM
    Espinet, P
    Redón, R
    [J]. ORGANOMETALLICS, 1999, 18 (26) : 5571 - 5576
  • [2] SUBSTITUTED OXINDOLES .I. PREPARATION AND SPECTRAL CHARACTERISTICS OF SOME SIMPLE OXINDOLE DERIVATIVES
    BECKETT, AH
    DAISLEY, RW
    WALKER, J
    [J]. TETRAHEDRON, 1968, 24 (19) : 6093 - &
  • [3] INTER VS INTRA-MOLECULAR AMIDOALKYLATIONS OF AROMATICS - NEW SYNTHESIS OF OXINDOLES, ISOQUINOLONES AND BENZAZEPINONES
    BENISHAI, D
    PELED, N
    SATATY, I
    [J]. TETRAHEDRON LETTERS, 1980, 21 (06) : 569 - 572
  • [4] Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature
    Boele, MDK
    van Strijdonck, GPF
    de Vries, AHM
    Kamer, PCJ
    de Vries, JG
    van Leeuwen, PWNM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) : 1586 - 1587
  • [5] SYNTHESIS OF OXINDOLES BY RADICAL CYCLIZATION
    BOWMAN, WR
    HEANEY, H
    JORDAN, BM
    [J]. TETRAHEDRON LETTERS, 1988, 29 (50) : 6657 - 6660
  • [6] NONTOXIC LIGANDS IN SAMARIUM DIIODIDE-MEDIATED CYCLIZATIONS
    CABRI, W
    CANDIANI, I
    COLOMBO, M
    FRANZOI, L
    BEDESCHI, A
    [J]. TETRAHEDRON LETTERS, 1995, 36 (06) : 949 - 952
  • [7] Cámpora J, 2001, ANGEW CHEM INT EDIT, V40, P3641, DOI 10.1002/1521-3773(20011001)40:19<3641::AID-ANIE3641>3.0.CO
  • [8] 2-9
  • [9] Cámpora J, 1999, ANGEW CHEM INT EDIT, V38, P147, DOI 10.1002/(SICI)1521-3773(19990115)38:1/2<147::AID-ANIE147>3.0.CO
  • [10] 2-I