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
  • [1] Enantioselective Palladium-Catalyzed Cascade Narasaka-Heck Cyclization/Suzuki Coupling Reaction
    Ye, Wenshao
    Cao, Kangning
    Ye, Zihao
    Qi, Shutao
    Yang, Junfeng
    Zhang, Junliang
    ACS CATALYSIS, 2025, 15 (03): : 2516 - 2521
  • [2] Enantioselective Aminosilylation of Alkenes by Palladium/Ming-Phos-Catalyzed Tandem Narasaka-Heck/Silylation Reaction
    Cao, Kangning
    Han, Jie
    Ye, Wenshao
    Hu, Dejun
    Ye, Zihao
    Yang, Junfeng
    Zhang, Junliang
    Chen, Fener
    ADVANCED SCIENCE, 2024, 11 (34)
  • [3] Regioselective synthesis of spirocyclic pyrrolines via a palladium-catalyzed Narasaka-Heck/C-H activation/[4+2] annulation cascade reaction
    Wei, Wan-Xu
    Kong, Xiangtao
    Jiao, Rui-Qiang
    Li, Xue-Song
    Wang, Cui-Tian
    Li, Yuke
    Liang, Yong-Min
    CHEMICAL SCIENCE, 2022, 13 (21) : 6348 - 6354
  • [4] Enantioselective Palladium-Catalyzed Direct Alkylation and Olefination Reaction of Simple Arenes
    Peng, Hong Mei
    Dai, Li-Xin
    You, Shu-Li
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (34) : 5826 - 5828
  • [5] Palladium-Catalyzed Electrochemical C-H Alkylation of Arenes
    Yang, Qi-Liang
    Li, Chuan-Zeng
    Zhang, Liang-Wei
    Li, Yu-Yan
    Tong, Xiaofeng
    Wu, Xin-Yan
    Mei, Tian-Sheng
    ORGANOMETALLICS, 2019, 38 (06) : 1208 - 1212
  • [6] Enantioselective difunctionalization of alkenes by a palladium-catalyzed Heck/borylation sequence
    Wu, Yuanqi
    Wu, Lizuo
    Zhang, Zhan-Ming
    Xu, Bing
    Liu, Yu
    Zhang, Junliang
    CHEMICAL SCIENCE, 2022, 13 (07) : 2021 - 2025
  • [7] Enantioselective Dicarbofunctionalization of Unactivated Alkenes by Palladium-Catalyzed Tandem Heck/Suzuki Coupling Reaction
    Zhang, Zhan-Ming
    Xu, Bing
    Wu, Lizuo
    Wu, Yuanqi
    Qian, Yanyan
    Zhou, Lujia
    Liu, Yu
    Zhang, Junliang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (41) : 14653 - 14659
  • [8] Experimental and Computational Studies of Palladium-Catalyzed Spirocyclization via a Narasaka-Heck/C(sp3 or sp2)-H Activation Cascade Reaction
    Wei, Wan-Xu
    Li, Yuke
    Wen, Ya-Ting
    Li, Ming
    Li, Xue-Song
    Wang, Cui-Tian
    Liu, Hong-Chao
    Xia, Yu
    Zhang, Bo-Sheng
    Jiao, Rui-Qiang
    Liang, Yong-Min
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (20) : 7868 - 7875
  • [9] Palladium-Catalyzed Oxidative Heck Coupling of Cyclic Enones with Simple Arenes by C-H Activation
    Chung, Leung Gulice Yiu
    Juwaini, Nur Asyikin Binte
    Seayad, Jayasree
    CHEMCATCHEM, 2015, 7 (08) : 1270 - 1274
  • [10] Palladium-Catalyzed C-H Alkynylation of Unactivated Alkenes
    Schreib, Benedikt S.
    Fadel, Marlene
    Carreira, Erick M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (20) : 7818 - 7822
12345