Pd(0)-Catalyzed Sequential C-N Bond Formation via Allylic and Aromatic C-H Amination of α-Methylstyrenes with Diaziridinone

被引:40
作者
Ramirez, Thomas A. [1 ]
Wang, Qian [1 ]
Zhu, Yingguang [1 ]
Zheng, Huaiji [1 ]
Peng, Xingao [1 ]
Cornwall, Richard G. [1 ]
Shi, Yian [1 ]
机构
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
基金
美国国家卫生研究院;
关键词
AEROBIC OXIDATIVE AMINATION; PD(II)-CATALYZED AMINATION; ASYMMETRIC-SYNTHESIS; TERMINAL ALKENES; PALLADIUM; DIAMINATION; ACTIVATION; REACTIVITY; AMIDATION; CARBON;
D O I
10.1021/ol401935c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel Pd(0)-catalyzed sequential C-N bond formation process via allylic and aromatic C-H amination of alpha-methylstyrenes with di-tert-butyldiaziridinone, giving spirocyclic indolines in good yields, is described. Four C-N bonds and one Spiro quaternary carbon are generated in a single operation.
引用
收藏
页码:4210 / 4213
页数:4
相关论文
共 102 条
  • [1] STRUCTURE OF A PHOSPHAZENE ANILINE COMPOUND
    ABBOUD, KA
    VILLANUEVA, LA
    BONCELLA, JM
    [J]. ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1993, 49 : 1848 - 1850
  • [2] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage
    Ackermann, Lutz
    Vicente, Ruben
    Kapdi, Anant R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9792 - 9826
  • [3] Akermark B., 2002, HDB ORGANOPALLADIUM, P1875
  • [4] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
    Alberico, Dino
    Scott, Mark E.
    Lautens, Mark
    [J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
  • [5] [Anonymous], 2004, Palladium Reagents andCatalysts
  • [6] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents
    Beccalli, Egle M.
    Broggini, Gianluigi
    Martinelli, Michela
    Sottocornola, Silvia
    [J]. CHEMICAL REVIEWS, 2007, 107 (11) : 5318 - 5365
  • [7] Insertion of arylsulfonylnitrene fragments into Pd-Pd bonds. Crystallographic characterization of the novel [Pd2Cl2(mu-dppm)(2)(mu-NSO2C6H4NO2-2)] A-frame adduct
    Besenyei, G
    Parkanyi, L
    Foch, I
    Simandi, LI
    Kalman, A
    [J]. CHEMICAL COMMUNICATIONS, 1997, (12) : 1143 - 1144
  • [8] A new and efficient palladium-catalyzed synthesis of a 2,3,4,5-tetrahydro-1H-2,4-benzodiazepine-1,3-dione derivative
    Bocelli, G
    Catellani, M
    Cugini, F
    Ferraccioli, R
    [J]. TETRAHEDRON LETTERS, 1999, 40 (13) : 2623 - 2624
  • [9] Synthesis and insertion reactions of the cyclometalated palladium-alkyl complexes Pd(CH2CMe2-o-C6H4)L2.: Observation of a pentacoordinated intermediate in the insertion of SO2
    Cámpora, J
    López, JA
    Palma, P
    del Rio, D
    Carmona, E
    Valerga, P
    Graiff, C
    Tiripicchio, A
    [J]. INORGANIC CHEMISTRY, 2001, 40 (17) : 4116 - 4126
  • [10] 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