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
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
  • [1] Palladium-catalyzed coupling of aryl bromides with aryl boranes, alkenes, and alkynes to produce byaryls, substituted alkenes, and alkynes.
    De, DBY
    Krogstad, DJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U197 - U197
  • [2] Ru(II)- or Rh(III)-Catalyzed Difunctionalization of Alkenes by Tandem Cyclization of N-Aryl Acrylamides with Alkenes
    Manoharan, Ramasamy
    Logeswaran, Ravichandran
    Jeganmohan, Masilamani
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (22): : 14830 - 14843
  • [3] Synthesis of 2-Pyridones and Iminoesters via Rh(III)-Catalyzed Oxidative Coupling between Acrylamides and Alkynes
    Su, Yan
    Zhao, Miao
    Han, Keli
    Song, Guoyong
    Li, Xingwei
    ORGANIC LETTERS, 2010, 12 (23) : 5462 - 5465
  • [4] Rh(III)-Catalyzed Oxidative Coupling of Unactivated Alkenes via C-H Activation
    Tsai, Andy S.
    Brasse, Mikael
    Bergman, Robert G.
    Ellman, Jonathan A.
    ORGANIC LETTERS, 2011, 13 (03) : 540 - 542
  • [5] Computational study on mechanism of Rh(III)-catalyzed oxidative Heck coupling of phenol carbamates with alkenes
    Zhang, Qi
    Yu, Hai-Zhu
    Li, Yi-Tong
    Liu, Lei
    Huang, Yong
    Fu, Yao
    DALTON TRANSACTIONS, 2013, 42 (12) : 4175 - 4184
  • [6] Rh(III)-catalyzed coupling of nitrones with alkynes for the synthesis of indolines
    Kong, Lingheng
    Xie, Fang
    Yu, Songjie
    Qi, Zisong
    Li, Xingwei
    CHINESE JOURNAL OF CATALYSIS, 2015, 36 (07) : 925 - 932
  • [7] Rh(III)-Catalyzed Tandem Oxidative Olefination-Michael Reactions between Aryl Carboxamides and Alkenes
    Wang, Fen
    Song, Guoyong
    Li, Xingwei
    ORGANIC LETTERS, 2010, 12 (23) : 5430 - 5433
  • [8] Synthesis of π-Extended Heterocycles via Rh(III)-Catalyzed Oxidative Annulation of 5-Aryl Pyrazinones with Alkynes
    Oh, Harin
    Byun, Hee Won
    Moon, Kyeongwon
    Kim, Saegun
    Ghosh, Prithwish
    An, Won
    Kwak, Jong Hwan
    Park, Jung Su
    Mishra, Neeraj Kumar
    Kim, In Su
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (23): : 16349 - 16360
  • [9] Rhodium(III)-Catalyzed Oxidative Coupling of 5-Aryl-1H-pyrazoles with Alkynes and Acrylates
    Li, Xingwei
    Zhao, Miao
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (20): : 8530 - 8536
  • [10] Rhodium-catalyzed annulative coupling of N-aryl-2-aminopyridine and propargylic amine via selective C-C and C-H bond activation
    He, Shiyu
    Yan, Xufei
    Lei, Yanxi
    Xiang, Haifeng
    Zhou, Xiangge
    CHEMICAL COMMUNICATIONS, 2020, 56 (15) : 2284 - 2287