Copper-Catalyzed Aerobic Oxidative C-H and C-C Functionalization of 1-[2-(Arylamino)aryl]ethanones Leading to Acridone Derivatives

被引:52
|
作者
Yu, Jipan [1 ]
Yang, Haijun [1 ]
Jiang, Yuyang [2 ]
Fu, Hua [1 ,2 ]
机构
[1] Tsinghua Univ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Dept Chem, Minist Educ, Beijing 100084, Peoples R China
[2] Tsinghua Univ, Grad Sch Shenzhen, Key Lab Chem Biol Guangdong Prov, Shenzhen 518057, Peoples R China
基金
中国国家自然科学基金;
关键词
C-C activation; C-H activation; cyclization; nitrogen heterocycles; synthetic methods; CROSS-COUPLING REACTIONS; ARYL BOND FORMATION; ONE-POT SYNTHESIS; N-ARYLATION; AMINO-ACIDS; PALLADIUM; ACTIVATION; AMINATION; ULLMANN; NITROGEN;
D O I
10.1002/chem.201204169
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Efficient copper-catalyzed aerobic oxidative C-H and C-C functionalization of 1-[2-(arylamino)aryl]ethanones leading to acridones has been developed. The procedure involves cleavage of aromatic C-H and acetyl C-C bonds with intramolecular formation of a diarylketone bond. The protocol uses inexpensive Cu(O2CCF3)(2) as catalyst, pyridine as additive, and economical and environmentally friendly oxygen as the oxidant, and the corresponding acridones with various functional groups were obtained in moderate to good yields.
引用
收藏
页码:4271 / 4277
页数:7
相关论文
共 50 条
  • [1] Copper-Catalyzed Aerobic Oxidative Cleavage of C-C Bonds in Epoxides Leading to Aryl Ketones
    Gu, Lijun
    Jin, Cheng
    Zhang, Hongtao
    Zhang, Lizhu
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (17): : 8453 - 8456
  • [2] Copper-Catalyzed Aerobic Oxidative Intramolecular C-H Amination Leading to Imidazobenzimidazole Derivatives
    Wang, Xiaoqiang
    Jin, Yunhe
    Zhao, Yufen
    Zhu, Lin
    Fu, Hua
    ORGANIC LETTERS, 2012, 14 (02) : 452 - 455
  • [3] Copper-catalyzed aerobic oxidative cleavage of C-C bonds in epoxides leading to aryl nitriles and aryl aldehydes
    Gu, Lijun
    Jin, Cheng
    CHEMICAL COMMUNICATIONS, 2015, 51 (30) : 6572 - 6575
  • [4] Copper-Catalyzed Aerobic Oxidative C-H Functionalization of Substituted Pyridines: Synthesis of Imidazopyridine Derivatives
    Yu, Jipan
    Jin, Yunhe
    Zhang, Hao
    Yang, Xiaobo
    Fu, Hua
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (49) : 16804 - 16808
  • [5] Copper-Catalyzed Aerobic Oxidative Functionalization of an Arene C-H Bond: Evidence for an Aryl-Copper(III) Intermediate
    King, Amanda E.
    Huffman, Lauren M.
    Casitas, Alicia
    Costas, Miguel
    Ribas, Xavi
    Stahl, Shannon S.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (34) : 12068 - 12073
  • [6] Recent Advances on Copper-Catalyzed C-C Bond Formation via C-H Functionalization
    Almasalma, Ahmad A.
    Mejia, Esteban
    SYNTHESIS-STUTTGART, 2020, 52 (18): : 2613 - 2622
  • [7] Copper-catalyzed oxidative C-H bond functionalization of N-allylbenzamide for C-N and C-C bond formation
    Ranjith, Jala
    Krishna, Palakodety Radha
    TETRAHEDRON LETTERS, 2019, 60 (21) : 1437 - 1440
  • [8] Copper-Catalyzed C-C Bond Formation through C-H Functionalization: Synthesis of Multisubstituted Indoles from N-Aryl Enaminones
    Bernini, Roberta
    Fabrizi, Giancarlo
    Sferrazza, Alessio
    Cacchi, Sandro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (43) : 8078 - 8081
  • [9] Progress and prospects in copper-catalyzed C-H functionalization
    Aneeja, Thaipparambil
    Neetha, Mohan
    Afsina, C. M. A.
    Anilkumar, Gopinathan
    RSC ADVANCES, 2020, 10 (57) : 34429 - 34458
  • [10] Copper-Catalyzed Aerobic Oxidative Intramolecular Alkene C-H Amination Leading to N-Heterocycles
    Lu, Juyou
    Jin, Yibao
    Liu, Hongxia
    Jiang, Yuyang
    Fu, Hua
    ORGANIC LETTERS, 2011, 13 (14) : 3694 - 3697