Palladium-Catalyzed C( sp3)- H Activation: A Facile Method for the Synthesis of 3,4-Dihydroquinolinone Derivatives**

被引:87
|
作者
Yan, Jia-Xuan [1 ,2 ]
Li, Hu [1 ,2 ]
Liu, Xiang-Wei [1 ,2 ]
Shi, Jiang-Ling [1 ,2 ]
Wang, Xin [1 ,2 ]
Shi, Zhang-Jie [1 ,2 ,3 ]
机构
[1] Peking Univ, PKU Green Chem Ctr, Beijing Natl Lab Mol Sci BNLMS, Beijing 100871, Peoples R China
[2] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Coll Chem, Beijing 100871, Peoples R China
[3] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
关键词
CH activation; dihydroquinolinones; palladacycles; palladium; synthetic methods; INTRAMOLECULAR ALKANE ARYLATION; PROTON-ABSTRACTION MECHANISM; BOND ACTIVATION; UNACTIVATED C(SP(3))-H; EFFICIENT SYNTHESIS; DIRECTING GROUP; FUNCTIONALIZATION; LIGAND; ACID; (HETERO)ARENES;
D O I
10.1002/anie.201402562
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
3,4-Dihydroquinolinones were synthesized by the palladium-catalyzed, oxidative-addition-initiated activation and arylation of inert C(sp(3))H bonds. Pd(OAc)(2) and P(o-tol)(3) were used as the catalyst and ligand, respectively, to improve the efficiency of the reaction. A further advantage of this reaction is that it could be performed in air. A relatively rare seven-membered palladacycle was proposed as a key intermediate of the catalytic cycle.
引用
收藏
页码:4945 / 4949
页数:5
相关论文
共 50 条
  • [41] Synergistic Palladium-Catalyzed C(sp3)?H Activation/C(sp3)?O Bond Formation: A Direct, Step-Economical Route to Benzolactones
    Novak, Petr
    Correa, Arkaitz
    Gallardo-Donaire, Joan
    Martin, Ruben
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (51) : 12236 - 12239
  • [42] Ring Construction by Palladium(0)-Catalyzed C(sp3)-H Activation
    Baudoin, Olivier
    ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (04) : 1114 - 1123
  • [43] Asymmetric Synthesis of β-Lactam via Palladium-Catalyzed Enantioselective Intramolecular C(sp3)-H Amidation
    Tong, Hua-Rong
    Zheng, Wenrui
    Lv, Xiaoyan
    He, Gang
    Liu, Peng
    Chen, Gong
    ACS CATALYSIS, 2020, 10 (01): : 114 - 120
  • [44] Synthesis of modified bile acids via palladium-catalyzed C(sp3)-H (hetero)arylation
    Borade, Somnath Arjun
    Naharwal, Sushma
    Bhambri, Himanshi
    Mandal, Sanjay K.
    Bajaj, Kiran
    Chitkara, Deepak
    Sakhuja, Rajeev
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (33) : 6719 - 6729
  • [45] Palladium-catalyzed synthesis of benzosilacyclobutenes via position-selective C(sp3)-H arylation
    Hamada, Naoya
    Hayashi, Daigo
    Shintani, Ryo
    CHEMICAL COMMUNICATIONS, 2023, 59 (59) : 9122 - 9125
  • [46] Palladium-Catalyzed Oxidative Carbonylation of Benzylic C-H Bonds via Nondirected C(sp3)-H Activation
    Xie, Pan
    Xie, Yinjun
    Qian, Bo
    Zhou, Han
    Xia, Chungu
    Huang, Hanmin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (24) : 9902 - 9905
  • [47] Palladium-catalyzed electrochemical C(sp3)-H acetoxylation of alcohol derivatives with an exo-directing group
    Ogawa, Daisuke
    Sasaki, Ayumu
    Kochi, Takuya
    Kakiuchi, Fumitoshi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (37) : 7696 - 7701
  • [48] The Emergence of Palladium-Catalyzed C(sp3)-H Functionalization of Free Carboxylic Acids
    Das, Animesh
    Maji, Biplab
    CHEMISTRY-AN ASIAN JOURNAL, 2021, 16 (05) : 397 - 408
  • [49] Palladium-Catalyzed Benzylic C(sp3)-H Carbonylative Arylation with Aryl Bromides
    Hu, Bowen
    Zhao, Haoqiang
    Wu, Yu
    Walsh, Patrick J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (23)
  • [50] Palladium-Catalyzed C(sp3)-H Nitrooxylation of Aliphatic Carboxamides with Practical Oxidants
    Liu, Xing
    Gao, Fang-Fang
    Xue, Yuan
    Luo, Jun
    Jiang, Chao
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (03): : 1417 - 1424