Easily Accessible Auxiliary for Palladium-Catalyzed Intramolecular Amination of C(sp2)-H and C(sp3)-H Bonds at δ- and ε-Positions

被引：142
作者：
Wang, Chao [1 ]
Chen, Changpeng [1 ]
Zhang, Jingyu [1 ]
Han, Jian [1 ]
Wang, Qian [1 ]
Guo, Kun [1 ]
Liu, Pei [1 ]
Guan, Mingyu [1 ]
Yao, Yingming [1 ]
Zhao, Yingsheng [1 ]
机构：
[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Jiangsu Prov Coll Chem, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 37期
关键词：
amination; CH activation; cyclization; heterocycles; palladium; C-H BONDS; DIRECTING GROUP; ACTIVATION; ARYLATION; FUNCTIONALIZATION; ALKYLATION; INDOLINES; CONSTRUCTION; DERIVATIVES; SELECTIVITY;
D O I：
10.1002/anie.201404854
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An easily synthesized and accessible N,O-bidentate auxiliary has been developed for selective CH activation under palladium catalysis. The novel auxiliary showed its first powerful application in CH functionalization of remote positions. Both C(sp(2))H and C(sp(3))H bonds at - and epsilon-positions were effectively activated, thus giving tetrahydroquinolines, benzomorpholines, pyrrolidines, and indolines in moderate to excellent yields by palladium-catalyzed intramolecular CH amination.
引用
收藏
页码：9884 / 9888
页数：5
相关论文
共 50 条
  • [21] Palladium-Catalyzed Amidation of Unactivated C(sp3)-H Bonds: from Anilines to Indolines
    Neumann, Julia J.
    Rakshit, Souvik
    Droege, Thomas
    Glorius, Frank
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (37) : 6892 - 6895
  • [22] Improved Protocol for Indoline Synthesis via Palladium-Catalyzed Intramolecular C(sp2)-H Amination
    He, Gang
    Lu, Chengxi
    Zhao, Yingsheng
    Nack, William A.
    Chen, Gong
    ORGANIC LETTERS, 2012, 14 (12) : 2944 - 2947
  • [23] Palladium-Catalyzed C(sp2)-H Activation for the Formation of C-N Bonds: Rapid Access to Benzimidazoquinazolines
    Guo, Xiaolong
    Hu, Jing
    Zhang, Mengmeng
    Wang, Luyao
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (03) : 417 - 421
  • [24] Modular synthesis of dihydro-isoquinolines: palladium-catalyzed sequential C(sp2)-H and C(sp3)-H bond activation
    Liu, Weidong
    Yu, Qingzhen
    Hu, Le'an
    Chen, Zenghua
    Huang, Jianhui
    CHEMICAL SCIENCE, 2015, 6 (10) : 5768 - 5772
  • [25] Pd-Catalyzed sequential β-C(sp3)-H arylation and intramolecular amination of δ-C(sp2)-H bonds for synthesis of quinolinones via an N,O-bidentate directing group
    Guan, Mingyu
    Pang, Yubo
    Zhang, Jingyu
    Zhao, Yingsheng
    CHEMICAL COMMUNICATIONS, 2016, 52 (43) : 7043 - 7046
  • [26] Pyridine-Directed Palladium-Catalyzed Phosphonation of C(sp2)-H Bonds
    Li, Changkun
    Yano, Takaaki
    Ishida, Naoki
    Murakami, Masahiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (37) : 9801 - 9804
  • [27] Palladium Catalyzed Arylation of C(sp3)-H Bonds of Carbonyl β-position in Water
    Luo Feihua
    Long Yang
    Li Zhengkai
    Zhou Xiangge
    ACTA CHIMICA SINICA, 2016, 74 (10) : 805 - 810
  • [28] Synthesis of Indolines by Palladium-Catalyzed Intermolecular Amination of Unactivated C(sp3)-H Bonds
    Sun, Xueliang
    Wu, Zhuo
    Qi, Weixin
    Ji, Xiaoming
    Cheng, Cang
    Zhang, Yanghui
    ORGANIC LETTERS, 2019, 21 (16) : 6508 - 6512
  • [29] Palladium-Catalyzed C-H Amination/[2+3] or [2+4] Cyclization via C(sp3 or sp2)-H Activation
    An, Yang
    Li, Yuke
    Zhang, Xiao-Yan
    Zhang, Zhe
    Gou, Xue-Ya
    Ding, Ya-Nan
    Li, Qiao
    Liang, Yong-Min
    ORGANIC LETTERS, 2021, 23 (20) : 7961 - 7965
  • [30] Palladium-Catalyzed γ-C(sp3)-H Arylation of Thiols by a Detachable Protecting/Directing Group
    Jin, Likun
    Wang, Jianchun
    Dong, Guangbin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (38) : 12352 - 12355
12345