Rh(III)-Catalyzed Oxidative Coupling of N-Aryl-2-aminopyridine with Alkynes and Alkenes

被引：212
|
作者：
Chen, Jinlei [2 ]
Song, Guoyong [1 ]
Pan, Cheng-Ling [1 ]
Li, Xingwei [1 ]
机构：
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
[2] Jilin Univ, State Key Lab Theoret & Computat Chem, Changchun 130023, Peoples R China
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 23期
关键词：
C-H BOND; INTERNAL ALKYNES; BENZOIC-ACIDS; ACTIVATION; RH; FUNCTIONALIZATION; CLEAVAGE; COUPLING/CYCLIZATION; CARBON; BENZAMIDES;
D O I：
10.1021/ol1022596
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[RhCp*Cl-2](2) (1-2 mol %) can catalyze the oxidative coupling of N-aryl-2-aminopyridines with alkynes and arylates to give N-(2-pyridyl)indoles and N-(2-pyridyl)quinolones, respectively, using Cu(OAc)(2) as an oxidant. Coupling with styrenes gave mono- and/or disubstituted olefination products.
引用
收藏
页码：5426 / 5429
页数：4
相关论文
共 50 条
  • [41] Oxidative Coupling of Aromatic Substrates with Alkynes and Alkenes under Rhodium Catalysis
    Satoh, Tetsuya
    Miura, Masahiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (37) : 11212 - 11222
  • [42] Ni-catalyzed, ZnCl2-assisted domino coupling of enones, alkynes, and alkenes
    Ikeda, S
    Sanuki, R
    Miyachi, H
    Miyashita, H
    Taniguchi, M
    Odashima, K
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (33) : 10331 - 10338
  • [43] Rh(III)-Catalyzed Annulation of 2-Biphenylboronic Acid with Diverse Activated Alkenes
    Liu, Bingxian
    Yang, Lingyun
    Dong, Zhenzhen
    Chang, Junbiao
    Li, Xingwei
    ORGANIC LETTERS, 2021, 23 (18) : 7199 - 7204
  • [44] Synthesis of 3-trifluoromethylindoles via Rh-catalyzed regioselective oxidative coupling of acetanilides with trifluoromethylated alkynes
    Zhou, Yirong
    Zhang, Chunyan
    Yuan, Jianjun
    Yang, Qin
    Xiao, Qiang
    Peng, Yiyuan
    TETRAHEDRON LETTERS, 2016, 57 (29) : 3222 - 3225
  • [45] Rhodium(III)-Catalyzed Oxidative Coupling of N-Phenylindole-3-carboxylic Acids with Alkenes and Alkynes via C4-H and C2-H/C2'-H Bond Cleavage
    Okada, Takeshi
    Sakai, Asumi
    Hinoue, Tomoaki
    Satoh, Tetsuya
    Hayashi, Yoshihiro
    Kawauchi, Susumu
    Chandrababunaidu, Kona
    Miura, Masahiro
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (10): : 5639 - 5649
  • [46] Synthesis of Functionalized α-Pyrone and Butenolide Derivatives by Rhodium-Catalyzed Oxidative Coupling of Substituted Acrylic Acids with Alkynes and Alkenes
    Mochida, Satoshi
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16): : 6295 - 6298
  • [47] Isoquinoline synthesis via rhodium-catalyzed oxidative cross-coupling/ cyclization of aryl aldimines and alkynes
    Guimond, Nicolas
    Fagnou, Keith
    Journal of the American Chemical Society, 2009, 131 (34): : 12050 - 12051
  • [48] Isoquinoline Synthesis via Rhodium-Catalyzed Oxidative Cross-Coupling/Cyclization of Aryl Aldimines and Alkynes
    Guimond, Nicolas
    Fagnou, Keith
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (34) : 12050 - +
  • [49] Rh-catalyzed aerobic oxidative cyclization of anilines, alkynes, and CO
    Li, Xinyao
    Pan, Jun
    Wu, Hao
    Jiao, Ning
    CHEMICAL SCIENCE, 2017, 8 (09) : 6266 - 6273
  • [50] Rh(III)-Catalyzed Cascade Oxidative Olefination/Cyclization of Picolinamides and Alkenes via C-H Activation
    Cai, Shangun
    Chen, Chao
    Shao, Peng
    Xi, Chanjuan
    ORGANIC LETTERS, 2014, 16 (11) : 3142 - 3145
12345