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
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
  • [31] Ruthenium(II) Biscarboxylate-Catalyzed Borylations of C(sp2)-H and C(sp3)-H Bonds
    De Sarkar, Suman
    Kumar, N. Y. Phani
    Ackermann, Lutz
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (01) : 84 - 87
  • [32] Copper-Catalyzed Intramolecular C(sp3)-H and C(sp2)-H Amidation by Oxidative Cyclization
    Wang, Zhen
    Ni, Jizhi
    Kuninobu, Yoichiro
    Kanai, Motomu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (13) : 3496 - 3499
  • [33] Transition-Metal-Catalyzed Acyloxylation: Activation of C(sp2)-H and C(sp3)-H Bonds
    Moghimi, Setareh
    Mahdavi, Mohammad
    Shafiee, Abbas
    Foroumadi, Alireza
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (20) : 3282 - 3299
  • [34] Intermolecular amidation of unactivated sp2 and sp3 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion
    Thu, Hung-Yat
    Yu, Wing-Yiu
    Che, Chi-Ming
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (28) : 9048 - 9049
  • [35] Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids:: Two distinct C-H activation pathways
    Chen, Xiao
    Goodhue, Charles E.
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12634 - 12635
  • [36] Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids: Two distinct C-H activation pathways
    Chen, Xiao
    Goodhue, Charles E.
    Yu, Jin-Quan
    Journal of the American Chemical Society, 2006, 128 (39): : 12634 - 12635
  • [37] Palladium-catalyzed unactivated β-methylene C(sp3)-H bond alkenylation of aliphatic amides and its application in a sequential C(sp3)-H/C(sp2)-H bond alkenylation
    Shan, Gang
    Huang, Guiyi
    Rao, Yu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (03) : 697 - 701
  • [38] Auxiliary-assisted palladium-catalyzed halogenation of unactivated C(sp3)-H bonds at room temperature
    Yang, Xinglin
    Sun, Yonghui
    Sun, Tian-yu
    Rao, Yu
    CHEMICAL COMMUNICATIONS, 2016, 52 (38) : 6423 - 6426
  • [39] 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
  • [40] An iron(ii)-based metalloradical system for intramolecular amination of C(sp2)-H and C(sp3)-H bonds: synthetic applications and mechanistic studies
    Das, Sandip Kumar
    Das, Subrata
    Ghosh, Supratim
    Roy, Satyajit
    Pareek, Monika
    Roy, Brindaban
    Sunoj, Raghavan B.
    Chattopadhyay, Buddhadeb
    CHEMICAL SCIENCE, 2022, 13 (40) : 11817 - 11828