Palladium-Catalyzed Enantioselective Narasaka-Heck Reaction/Direct C-H Alkylation of Arenes: Iminoarylation of Alkenes

被引：91
|
作者：
Bao, Xu [1 ]
Wang, Qian [1 ]
Zhu, Jieping [1 ]
机构：
[1] Ecole Polytech Fed Lausanne, Inst Chem Sci & Engn, LSPN, SB,ISIC, BCH 5304, CH-1015 Lausanne, Switzerland
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 32期
基金：
瑞士国家科学基金会;
关键词：
asymmetric catalysis; C-H activation; dihydropyrroles; domino reactions; Narasaka-Heck reactions; C(SP(2))-H BOND ACTIVATION; ASYMMETRIC HECK; EFFICIENT SYNTHESIS; OXIME ESTERS; CYCLIZATION; DERIVATIVES; DIHYDROPYRROLES; 1-AZAAZULENES; AMINATION; ARYLATION;
D O I：
10.1002/anie.201705641
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A palladium-catalyzed reaction of gamma,delta-unsaturated oxime esters with oxadiazoles afforded dihydropyrroles in good to excellent yields through an intramolecular iminopalladation/intermolecular direct heteroarene C-H alkylation cascade. This unprecedented iminoarylation of alkenes was subsequently realized in an enantioselective manner in the presence of a chiral bidentate phosphine ligand (Synphos).
引用
收藏
页码：9577 / 9581
页数：5
相关论文
共 50 条
  • [41] Palladium-Catalyzed Aryl C-H Olefination with Unactivated, Aliphatic Alkenes
    Deb, Arghya
    Bag, Sukdev
    Kancherla, Rajesh
    Maiti, Debabrata
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (39) : 13602 - 13605
  • [42] Palladium-Catalyzed Enantioselective Domino Heck/Intermolecular C-H Bond Functionalization: Development and Application to the Synthesis of (+)-Esermethole
    Kong, Wangqing
    Wang, Qian
    Zhu, Jieping
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (51) : 16028 - 16031
  • [43] Enantioconvergent Palladium-Catalyzed Alkylation of Tertiary Allylic C-H Bonds
    Nong, Zhong-Sheng
    Chen, Xin-Ran
    Wang, Pu-Sheng
    Hong, Xin
    Gong, Liu-Zhu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (46)
  • [44] Mechanistic Study of Palladium-Catalyzed Oxidative C-H/C-H Coupling of Polyfluoroarenes with Simple Arenes
    Tang, Shi-ya
    Yu, Hai-zhu
    You, Wan-li
    Guo, Qing-xiang
    CHINESE JOURNAL OF CHEMICAL PHYSICS, 2013, 26 (04) : 415 - 423
  • [45] Palladium-catalysed branch- and enantioselective allylic C-H alkylation of α-alkenes
    Nong, Zhong-Sheng
    Zhu, Ling
    Wang, Tian-Ci
    Fan, Lian-Feng
    Wang, Pu-Sheng
    Gong, Liu-Zhu
    NATURE SYNTHESIS, 2022, 1 (06): : 487 - 496
  • [46] Monodentate Phosphorus Ligand-Enabled General Palladium-Catalyzed Allylic C-H Alkylation of Terminal Alkenes
    Fan, Lian-Feng
    Wang, Pu-Sheng
    Gong, Liu-Zhu
    ORGANIC LETTERS, 2019, 21 (17) : 6720 - 6725
  • [47] Palladium-Catalyzed Enantioselective Allylic Alkylations through C-H Activation
    Trost, Barry M.
    Thaisrivongs, David A.
    Donckele, Etienne J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (05) : 1523 - 1526
  • [48] Palladium-catalyzed tandem Heck reaction/C-H functionalization - Preparation of spiro-indane-oxindoles
    Ruck, Rebecca T.
    Huffman, Mark A.
    Kim, Mary M.
    Shevlin, Michael
    Kandur, Wynne V.
    Davies, Ian W.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (25) : 4711 - 4714
  • [49] Palladium-Catalyzed Enantioselective C-H Aminocarbonylation: Synthesis of Chiral Isoquinolinones
    Han, Hui
    Zhang, Tao
    Yang, Shang-Dong
    Lan, Yu
    Xia, Ji-Bao
    ORGANIC LETTERS, 2019, 21 (06) : 1749 - 1754
  • [50] Palladium-Catalyzed Regiocontrollable Reductive Heck Reaction of Unactivated Aliphatic Alkenes
    Wang, Chengdong
    Xiao, Guanlin
    Guo, Tao
    Ding, Yalan
    Wu, Xiaojin
    Loh, Teck-Peng
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (30) : 9332 - 9336
12345