Copper-promoted ortho-directed C-H amination of 2-arylpyridines with NH-heterocycles

被引:0
|
作者
Zeng, Yang-Hao [1 ,2 ]
Dong, Lin [1 ,2 ]
机构
[1] Sichuan Univ, Sichuan Engn Lab Plant Sourced Drug, Key Lab Drug Targeting & Drug Delivery Syst Educ M, West China Sch Pharm, Chengdu 610041, Peoples R China
[2] Sichuan Univ, Sichuan Res Ctr Drug Precis Ind Technol, West China Sch Pharm, Chengdu 610041, Peoples R China
关键词
AMIDATION; ARYLATION; PYRAZOLE; ARENES; BONDS; SITE;
D O I
10.1039/d4ob01126k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper-mediated C-N coupling of azaheterocycles with aryl C-H bonds has been realized for the synthesis of N-(hetero)arylated heteroarenes. This method is characterized by high regioselectivity, atom economy and a wide substrate scope of 2-arylazines and azaheterocycles. The corresponding C-N coupling products were shown to undergo further transformation to synthesize more complex molecules.
引用
收藏
页码:7390 / 7394
页数:5
相关论文
共 50 条
  • [1] N-Aminopyridinium Ylide-Directed, Copper-Promoted Amination of sp2 C-H Bonds
    Kwak, Se Hun
    Daugulis, Olafs
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (20): : 13022 - 13032
  • [2] Identification of monodentate oxazoline as a ligand for copper-promoted ortho-C-H hydroxylation and amination
    Shang, Ming
    Shao, Qian
    Sun, Shang-Zheng
    Chen, Yan-Qiao
    Xu, Hui
    Dai, Hui-Xiong
    Yu, Jin-Quan
    CHEMICAL SCIENCE, 2017, 8 (02) : 1469 - 1473
  • [3] Water as a Hydroxy Source in a RhIII-Catalyzed Directed C-H Hydroxylation of 2-Arylpyridines
    Kim, Kiseong
    Hyun, Jaeyong
    Kim, Jin
    Kim, Hyunwoo
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (07) : 907 - 912
  • [4] Rhodium-catalysed direct ortho arylation of 2-arylpyridines with arylstannanes via C-H activation
    Oi, S
    Fukita, S
    Inoue, Y
    CHEMICAL COMMUNICATIONS, 1998, (22) : 2439 - 2440
  • [5] Functionalizations of Aryl C-H Bonds in 2-Arylpyridines via Sequential Borylation and Copper Catalysis
    Niu, Liting
    Yang, Haijun
    Yang, Daoshan
    Fu, Hua
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (11-12) : 2211 - 2217
  • [6] Copper-Promoted Sulfenylation of sp2 C-H Bonds
    Ly Dieu Tran
    Popov, Ilya
    Daugulis, Olafs
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (44) : 18237 - 18240
  • [7] Palladium catalyzed direct ortho C-H acylation of 2-arylpyridines using toluene derivatives as acylation reagents
    Xu, Zhipeng
    Xiang, Biao
    Sun, Peipei
    RSC ADVANCES, 2013, 3 (06) : 1679 - 1682
  • [8] Copper-promoted C-H bond functionalization for heterocycle synthesis
    Hung Tran-Vu
    Popov, Ilya
    Daugulis, Olafs
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [9] Copper-Promoted Double Oxidative C-H Amination Cascade for the Synthesis of Imidazo[1,5-a]quinolines
    Li, Zhong
    Wu, Song-Song
    Luo, Zai-Gang
    Liu, Wei-Kang
    Feng, Cheng-Tao
    Ma, Shi-Tang
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (10): : 4386 - 4392
  • [10] Copper(II)-Catalyzed Ortho-Acyloxylation of the 2-Arylpyridines sp2 C-H Bonds with Anhydrides, Using O2 as Terminal Oxidant
    Wang, Wenhui
    Luo, Fang
    Zhang, Shouhui
    Cheng, Jiang
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (07): : 2415 - 2418