Copper-Catalyzed Dehydrogenative Cross-Coupling of Benzothiazoles with Thiazoles and Polyfluoroarene

被引：99
作者：
Fan, Shilu [1 ]
Chen, Zhao [2 ]
Zhang, Xingang [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
[2] SW Petr Univ, Sch Chem & Chem Engn, Chengdu 610500, Sichuan, Peoples R China
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 18期
关键词：
C-H FUNCTIONALIZATION; ELECTRON-DEFICIENT POLYFLUOROARENES; BOND FORMATION; DIRECT ARYLATION; GENERAL-METHOD; SIMPLE ARENES; INDOLES; ACTIVATION; EFFICIENT; AZOLES;
D O I：
10.1021/ol3023165
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A copper-catalyzed dehydrogenative cross-coupling of benzothiazoles with thiazoles and polyfluoroarene under mild reaction conditions is described. This protocol provides a straightforward and operationally simple method for the synthesis of the 2,2'-linkage of thiazoles and 2-polyfluoroarylthiazoles of interest in life and material sciences.
引用
收藏
页码：4950 / 4953
页数：4
相关论文
共 81 条
  • [1] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage
    Ackermann, Lutz
    Vicente, Ruben
    Kapdi, Anant R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9792 - 9826
  • [2] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
    Alberico, Dino
    Scott, Mark E.
    Lautens, Mark
    [J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
  • [3] C-F Bond Activation in Organic Synthesis
    Amii, Hideki
    Uneyama, Kenji
    [J]. CHEMICAL REVIEWS, 2009, 109 (05) : 2119 - 2183
  • [4] Fluorinated organic materials for electronic and optoelectronic applications: the role of the fluorine atom
    Babudri, Francesco
    Farinola, Gianluca M.
    Naso, Francesco
    Ragni, Roberta
    [J]. CHEMICAL COMMUNICATIONS, 2007, (10) : 1003 - 1022
  • [5] Thiopeptide antibiotics
    Bagley, MC
    Dale, JW
    Merritt, EA
    Xiong, A
    [J]. CHEMICAL REVIEWS, 2005, 105 (02) : 685 - 714
  • [6] Copper-mediated C-H bond arylation of arenes with arylboronic acids
    Ban, Ikuya
    Sudo, Tomoko
    Taniguchi, Tadashi
    Itami, Kenichiro
    [J]. ORGANIC LETTERS, 2008, 10 (16) : 3607 - 3609
  • [7] Copper-Catalyzed C-C Bond Formation through C-H Functionalization: Synthesis of Multisubstituted Indoles from N-Aryl Enaminones
    Bernini, Roberta
    Fabrizi, Giancarlo
    Sferrazza, Alessio
    Cacchi, Sandro
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (43) : 8078 - 8081
  • [8] Twofold C-H functionalization:: Palladium-catalyzed ortho arylation of anilides
    Brasche, Gordon
    Garcia-Fortanet, Jorge
    Buchwald, Stephen L.
    [J]. ORGANIC LETTERS, 2008, 10 (11) : 2207 - 2210
  • [9] C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines
    Brasche, Gordon
    Buchwald, Stephen L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) : 1932 - 1934
  • [10] A facile, metal- and solvent-free, autoxidative coupling of quinolines with indoles and pyrroles
    Brasse, Mikael
    Ellman, Jonathan A.
    Bergman, Robert G.
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (17) : 5019 - 5021
123456789