Oxidative Copper-Catalyzed Regioselective Trifluoromethylation of Fused Imidazo[1,5-a]-N-heteroarenes using Langlois Reagent

被引:10
|
作者
Sandeep, Mummadi [1 ,2 ]
Shantharjun, Bangarigalla [1 ,2 ]
Kumar, Geetala Pradeep [1 ,3 ]
Reddy, Kallu Rajender [1 ,2 ,3 ]
机构
[1] Indian Inst Chem Technol, CSIR, Catalysis & Fine Chem Div, Hyderabad 500007, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, UP, India
[3] IICT, CSIR, IICT RMIT Joint Res Ctr, Hyderabad 500007, India
关键词
Copper; Homogeneous catalysis; Langlois reagent; Nitrogen heterocycles; Trifluoromethylation; C-H AMINATION; FLUORINE; ACCESS; CYCLIZATION; FORMAMIDES; 1,7-ENYNES; ACTIVATION; CASCADE; POTENT;
D O I
10.1002/ejoc.202001266
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple, mild, and efficient oxidative copper-catalyzed regioselective trifluoromethylation of imidazo[1,5-a]-N-heteroarenes have been developed using Langlois(,) (NaSO2CF3) reagent as CF3 source. This method gives biologically relevant trifluoromethylated fused imidazoles in moderate to good yields with good functional group tolerance. The key features of the reaction are mild conditions, short reaction time, and room temperature reaction.
引用
收藏
页码:246 / 252
页数:7
相关论文
共 50 条
  • [21] Visible-Light-Induced Copper-Catalyzed Decarboxylative Coupling of Redox-Active Esters with N-Heteroarenes
    Lyu, Xue-Li
    Huang, Shi-Sheng
    Song, Hong-Jian
    Liu, Yu-Xiu
    Wang, Qing-Min
    ORGANIC LETTERS, 2019, 21 (14) : 5728 - 5732
  • [22] Ruthenium(II)-Catalyzed Regioselective 1,2-Hydrosilylation of N-Heteroarenes and Tetrel Bonding Mechanism
    Behera, Deepak
    Thiyagarajan, Subramanian
    Anjalikrishna, Puthannur K.
    Suresh, Cherumuttathu H.
    Gunanathan, Chidambaram
    ACS CATALYSIS, 2021, 11 (10): : 5885 - 5893
  • [23] Palladium-catalyzed Highly Regioselective C-3 Arylation of Imidazo[1,5-a]pyridine
    Huang, Chunhui
    Giokaris, Alexandros
    Gevorgyan, Vladimir
    CHEMISTRY LETTERS, 2011, 40 (09) : 1053 - 1054
  • [24] Copper-Catalyzed Synthesis of 3-Aryl-9H-imidazo[1,5-a]indol-9-ones Using Oxygen as the Sole Oxidant
    Chen, Yufeng
    Yang, Ruitong
    Xiao, Fuhong
    Xu, Tianci
    Mao, Guojiang
    Deng, Guo-Jun
    ORGANIC LETTERS, 2023, 25 (20) : 3702 - 3707
  • [25] Regioselective 1,2-hydroboration of N-heteroarenes using a potassium-based catalyst
    Liu, Tianwei
    He, Jianghua
    Zhang, Yuetao
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (15): : 2749 - 2755
  • [26] Copper-Catalyzed Regioselective Oxytrifluoromethylation of Allenes Using a CF3-Transfer Reagent
    Wang, Yanan
    Jiang, Min
    Liu, Jin-Tao
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (14-15) : 2907 - 2912
  • [27] Copper-Catalyzed C4-H Regioselective Phosphorylation/Trifluoromethylation of Free 1-Naphthylamines
    Jing, Chunfeng
    Chen, Xiaolan
    Sun, Kai
    Yang, Yongkang
    Chen, Tong
    Liu, Yan
    Qu, Lingbo
    Zhao, Yufen
    Yu, Bing
    ORGANIC LETTERS, 2019, 21 (02) : 486 - 489
  • [28] Regioselective synthesis of imidazo[1,5-a]quinoxalines and methyl N-phenylbenzimidats on an ionic liquid support
    Chen, Li-Hsun
    Kao, Chih-Hsien
    Dhole, Sandip
    Barve, Indrajeet J.
    Shen, Li-Ching
    Chung, Wen-Sheng
    Sun, Chung-Ming
    RSC ADVANCES, 2016, 6 (80): : 76123 - 76127
  • [29] Regioselective copper-catalyzed N(1)-(hetero)-arylation of protected histidine
    Sharma, Krishna K.
    Mandloi, Meenakshi
    Jain, Rahul
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (38) : 8937 - 8941
  • [30] Copper-Catalyzed Oxidative Cross-Coupling of N,N-Dimethylanilines with Heteroarenes under Molecular Oxygen
    Huang, Lehao
    Niu, Tianmin
    Wu, Jun
    Zhang, Yuhong
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (06): : 1759 - 1766