Selective C4-F bond cleavage/C-O bond formation of polyfluoroarenes with phenols and benzyl alcohols

被引:20
作者
Liu, Cuibo [1 ,2 ]
Cao, Liming [1 ,2 ]
Yin, Xuguang [1 ,2 ]
Xu, Haolan [3 ]
Zhang, Bin [1 ,2 ]
机构
[1] Tianjin Univ, Coinnovat Ctr Chem & Chemcial Engn Tianjin, Sch Sci, Dept Chem, Tianjin 300072, Peoples R China
[2] Minist Educ, Key Lab Syst Bioengn, Tianjin 300072, Peoples R China
[3] Univ S Australia, Ian Work Res Inst, Mawson Lakes, SA 5095, Australia
基金
中国国家自然科学基金;
关键词
Polyfluoroarenes; C-F bond cleavage; C-O bond formation; Phenols; Benzyl alcohols; C-H BOND; COPPER-CATALYZED ARYLATION; ULLMANN-TYPE SYNTHESIS; ARYL HALIDES; F ACTIVATION; LIGAND-FREE; DIARYL ETHER; N-ARYLATION; FLUORINE; EFFICIENT;
D O I
10.1016/j.jfluchem.2013.08.013
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A facile and efficient SNAr method for the synthesis of unsymmetrical polyfluoroaryl ethers via selective C4-F bond cleavage of pentafluorobenzene is reported. The reaction could proceed smoothly without the requirement of additional metals or ligands, and afford a series of the corresponding products in good to high yields. A wide variety of substituted phenols and alcohols provided 1,2,4,5-tetrafluoropheny ether derivatives in regioselective manner. (C) 2013 Elsevier B.V. All rights reserved.
引用
收藏
页码:51 / 60
页数:10
相关论文
共 94 条
  • [1] Nucleophilic aryloxydefluorination of pentafluorobenzene without noble metal catalysis
    Adonin, Nicolay Yu.
    Bardin, Vadim V.
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2013, 153 : 165 - 167
  • [2] Cu-catalyzed N- and O-arylation of 2-, 3-, and 4-hydroxypyridines and hydroxyquinolines
    Altman, Ryan A.
    Buchwald, Stephen L.
    [J]. ORGANIC LETTERS, 2007, 9 (04) : 643 - 646
  • [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] Copper(0) in the Ullmann heterocycle-aryl ether synthesis of 4-phenoxypyridine using multimode microwave heating
    Benaskar, Faysal
    Engels, Volker
    Patil, Narendra
    Rebrov, Evgeny V.
    Meuldijk, Jan
    Hessel, Volker
    Hulshof, Lumbertus A.
    Jefferson, David A.
    Schouten, Jaap C.
    Wheatley, Andrew E. H.
    [J]. TETRAHEDRON LETTERS, 2010, 51 (02) : 248 - 251
  • [6] POLYFLUOROARENES .5. PENTAFLUOROPHENYLHYDRAZINE AND PENTAFLUOROPHENYL RADICAL
    BIRCHALL, JM
    HASZELDINE, RN
    PARKINSON, AR
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1962, (DEC): : 4966 - &
  • [7] Routes to fluorinated organic derivatives by nickel mediated C-F activation of heteroaromatics
    Braun, T
    Perutz, RN
    [J]. CHEMICAL COMMUNICATIONS, 2002, (23) : 2749 - 2757
  • [8] Catalytic C-F activation of polyfluorinated pyridines by nickel-mediated cross-coupling reactions
    Braun, T
    Perutz, RN
    Sladek, MI
    [J]. CHEMICAL COMMUNICATIONS, 2001, (21) : 2254 - 2255
  • [9] C-F Bond Activation of Highly Fluorinated Molecules at Rhodium: From Model Reactions to Catalysis
    Braun, Thomas
    Wehmeier, Falk
    [J]. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2011, (05) : 613 - 625
  • [10] AROMATIC POLYFLUORO-COMPOUNDS .4. THE REACTION OF AROMATIC POLYFLUORO-COMPOUNDS WITH NITROGEN-CONTAINING BASES
    BROOKE, GM
    BURDON, J
    STACEY, M
    TATLOW, JC
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1960, (APR): : 1768 - 1771