Rhodium(III)-Catalyzed Oxidative C-H Coupling of N-Methoxybenzamides with Aryl Boronic Acids: One-Pot Synthesis of Phenanthridinones

被引:152
|
作者
Karthikeyan, Jaganathan [1 ]
Haridharan, Radhakrishnan [1 ]
Cheng, Chien-Hong [1 ]
机构
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
关键词
C-H activation; cross-coupling; homogeneous catalysis; phenanthridinones; rhodium; CATALYZED DIRECT ARYLATION; CARBON-HYDROGEN BONDS; INTERNAL ALKYNES; ISOQUINOLINIUM SALTS; ARYLBORON REAGENTS; ROOM-TEMPERATURE; ACTIVATION; CLEAVAGE; FUNCTIONALIZATION; MULTIPLE;
D O I
10.1002/anie.201206890
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
General solution: An efficient rhodium-catalyzed dual CiH bond activation and cyclization of N-methoxybenzamides 1 with aryl boronic acids 2 (see scheme; Cp=Me5C5) provides a straightforward and general approach to the phenanthridinone structure, which occurs widely in natural products and drugs. Highly regioselective CiC and CiN bond formation under mild conditions afforded a wide range of substituted phenanthridinones 3. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:12343 / 12347
页数:5
相关论文
共 50 条
  • [1] Rhodium(III)-Catalyzed Annulation of N-Methoxybenzamides with Heterobicyclic Alkenes by C-H Functionalization: Synthesis of Benzo[b]phenanthridinones
    Cheng, Ying
    Parthasarathy, Kanniyappan
    Bolm, Carsten
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (08) : 1203 - 1206
  • [2] Synthesis of Phenanthridinones from N-Methoxybenzamides and Arenes by Multiple Palladium-Catalyzed C-H Activation Steps at Room Temperature
    Karthikeyan, Jaganathan
    Cheng, Chien-Hong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (42) : 9880 - 9883
  • [3] One-pot sequential reaction to 2-substituted-phenanthridinones from N-methoxybenzamides
    Liang, Dongdong
    Sersen, Deanna
    Yang, Chao
    Deschamps, Jeffrey R.
    Imler, Gregory H.
    Jiang, Chao
    Xue, Fengtian
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (20) : 4390 - 4398
  • [4] One-Pot Formation of C-C and C-N Bonds through Palladium-Catalyzed Dual C-H Activation: Synthesis of Phenanthridinones
    Wang, Guan-Wu
    Yuan, Ting-Ting
    Li, Dan-Dan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (06) : 1380 - 1383
  • [5] Rhodium-catalyzed regioselective direct C-H arylation of indoles with aryl boronic acids
    Wang, Liang
    Qu, Xing
    Li, Zhan
    Peng, Wang-Ming
    TETRAHEDRON LETTERS, 2015, 56 (24) : 3754 - 3757
  • [6] Synthesis of 3-Methyleneisoindolin-1-ones via Rhodium(III)-Catalyzed C-H/N-H Activation and Annulation of N-Methoxybenzamides with Potassium Vinyltrifluoroborate
    Kumar, Vikash
    Gandeepan, Parthasarathy
    CHEMISTRY-AN ASIAN JOURNAL, 2024, 19 (22)
  • [7] One-Pot Synthesis of Highly Substituted Polyheteroaromatic Compounds by Rhodium(III)-Catalyzed Multiple C-H Activation and Annulation
    Jayakumar, Jayachandran
    Parthasarathy, Kanniyappan
    Chen, Yi-Hsiang
    Lee, Tai-Hua
    Chuang, Shih-Ching
    Cheng, Chien-Hong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (37) : 9889 - 9892
  • [8] Rhodium(III)-catalyzed Oxidative Coupling of N-Methoxybenzamides and Ethenesulfonyl fluoride: a C-H Bond Activation Strategy for the Preparation of 2-Aryl ethenesulfonyl fluorides and Sulfonyl fluoride Substituted γ-Lactams
    Wang, Shi-Meng
    Li, Chen
    Leng, Jing
    Bukhari, Syed Nasir Abbas
    Qin, Hua-Li
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (09): : 1411 - 1415
  • [9] Synthesis of isoindolinones via palladium-catalyzed C-H activation of N-methoxybenzamides
    Li, Dan-Dan
    Yuan, Ting-Ting
    Wang, Guan-Wu
    CHEMICAL COMMUNICATIONS, 2011, 47 (48) : 12789 - 12791
  • [10] Ruthenium-Catalyzed Oxidative C-H Bond Olefination of N-Methoxybenzamides Using an Oxidizing Directing Group
    Li, Bin
    Ma, Jianfeng
    Wang, Nuancheng
    Feng, Huiliang
    Xu, Shansheng
    Wang, Baiquan
    ORGANIC LETTERS, 2012, 14 (03) : 736 - 739