A General Direct Arylation of Polyfluoroarenes with Heteroaryl and Aryl Chlorides Catalyzed by Palladium Indolylphosphine Complexes

被引:21
|
作者
Yuen, On Ying [1 ,2 ]
Charoensak, Mueangkaew [3 ,4 ]
So, Chau Ming [1 ,2 ]
Kuhakarn, Chutima [3 ,4 ]
Kwong, Fuk Yee [1 ,2 ]
机构
[1] Hong Kong Polytech Univ, State Key Lab Chirosci, Kowloon, Hong Kong, Peoples R China
[2] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Kowloon, Hong Kong, Peoples R China
[3] Mahidol Univ, Fac Sci, Dept Chem, Bangkok 10400, Thailand
[4] Mahidol Univ, Fac Sci, Ctr Excellence Innovat Chem PERCH CIC, Bangkok 10400, Thailand
关键词
aryl chlorides; CH arylation; palladium; phosphine; polyfluoroarenes; CROSS-COUPLING REACTIONS; ELECTRON-DEFICIENT POLYFLUOROARENES; PHOSPHINE-LIGANDS; MESYLATES; HALIDES; HETEROCYCLES; PRECATALYST; SELECTIVITY; ACTIVATION; DISCOVERY;
D O I
10.1002/asia.201500048
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first general examples of direct coupling of heteroaryl chlorides, especially substituted 2-pyridyl chlorides which were previously found to be problematic, with electron-deficient polyfluoroarenes are reported. Pd(OAc)(2) associated with 3-(dicyclohexylphosphino)-2-phenylindole L1 serves as the effective catalyst which allows the challenging direct coupling of heteroaryl chlorides and polyfluoroarenes. In addition to heterocycles, a wide range of non-activated and activated aryl chlorides and alkenyl chlorides were also applicable under this catalyst system. A catalyst loading down to 1mol% Pd can be achieved.
引用
收藏
页码:857 / 861
页数:5
相关论文
共 50 条
  • [21] Palladium-Catalyzed Direct Arylation of Electron-Deficient Polyfluoroarenes with Arylboronic Acids
    Wei, Ye
    Kan, Jian
    Wang, Min
    Su, Weiping
    Hong, Maochun
    [J]. ORGANIC LETTERS, 2009, 11 (15) : 3346 - 3349
  • [22] A general method for the direct α-arylation of aldehydes with aryl bromides and chlorides
    Martin, Ruben
    Buchwald, Stephen L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (38) : 7236 - 7239
  • [23] Palladium-catalyzed direct arylation of phenols with aryl iodides
    Long, Rongrong
    Yan, Xufei
    Wu, Zhiqing
    Li, Zhengkai
    Xiang, Haifeng
    Zhou, Xiangge
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (12) : 3571 - 3574
  • [24] Palladium-catalyzed direct arylation of thiazoles with aryl bromides
    Yokooji, A
    Okazawa, T
    Satoh, T
    Miura, M
    Nomura, M
    [J]. TETRAHEDRON, 2003, 59 (30) : 5685 - 5689
  • [25] Palladium-Catalyzed Direct Arylation of Heteroarenes with Aryl Mesylates
    So, Chau Ming
    Lau, Chak Po
    Kwong, Fuk Yee
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (03) : 761 - 765
  • [26] Palladium-catalyzed C-H bond arylation with aryl chlorides
    Chiong, Hendrich A.
    Daugulis, Olafs
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [27] Palladium-catalyzed arylation of electron-rich heterocycles with aryl chlorides
    Chiong, Hendrich A.
    Daugulis, Olafs
    [J]. ORGANIC LETTERS, 2007, 9 (08) : 1449 - 1451
  • [28] Efficient palladium-catalyzed N-arylation of a sulfoximine with aryl chlorides
    Yongpruksa, Nattawut
    Calkins, Nathan L.
    Harmata, Michael
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (27) : 7665 - 7667
  • [29] PALLADIUM CATALYZED OLEFIN ARYLATION - EXTENDING THE SCOPE OF THE HECK REACTION TO ARYL CHLORIDES
    DAVISON, JB
    SIMON, NM
    SOJKA, SA
    [J]. JOURNAL OF MOLECULAR CATALYSIS, 1984, 22 (03): : 349 - 352
  • [30] A General Palladium-Catalyzed Sonogashira Coupling of Aryl and Heteroaryl Tosylates
    R'kyek, Omar
    Halland, Nis
    Lindenschmidt, Andreas
    Alonso, Jorge
    Lindemann, Peter
    Urmann, Matthias
    Nazare, Marc
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (33) : 9986 - 9989