Facile Synthesis of Polycyclic Aromatic Hydrocarbons: BrOnsted Acid Catalyzed Dehydrative Cycloaromatization of Carbonyl Compounds in 1,1,1,3,3,3-Hexafluoropropan-2-ol

被引：41
作者：
Fujita, Takeshi [1 ]
Takahashi, Ikko [1 ]
Hayashi, Masaki [1 ]
Wang, Jingchen [1 ]
Fuchibe, Kohei [1 ]
Ichikawa, Junji [1 ]
机构：
[1] Univ Tsukuba, Div Chem, Fac Pure & Appl Sci, Tsukuba, Ibaraki 3058571, Japan
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 02期
基金：
日本学术振兴会;
关键词：
Aromatization; BrOnsted acids; Cyclization; Hydrocarbons; Polycycles; CRAFTS-TYPE CYCLIZATION; FLUORINATED ALCOHOLS; GRAPHITE RIBBONS; ACTIVATION; SUBSTITUENT; PHENACENES; 1,1-DIFLUORO-1-ALKENES; PHENANTHRENES; ENHANCEMENT; METABOLITES;
D O I：
10.1002/ejoc.201601406
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The cycloaromatization of aromatic aldehydes and ketones was readily achieved by using a BrOnsted acid catalyst in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP). In the presence of a catalytic amount of trifluoromethanesulfonic acid, biaryl-2-ylacetaldehydes and 2-benzylbenzaldehydes underwent sequential intramolecular cationic cyclization and dehydration to afford phenacenes and acenes, respectively. Furthermore, biaryl-2-ylacetaldehydes bearing a cyclopentene moiety at the -position underwent unprecedented cycloaromatization including ring expansion to afford triphenylenes. HFIP effectively promoted the cyclizations by suppressing side reactions presumably as a result of stabilization of the cationic intermediates.
引用
收藏
页码：262 / 265
页数：4
相关论文
共 64 条
  • [11] Champagne, 2014, ANGEW CHEM, V126, P14055, DOI DOI 10.1002/ANGE.201406088
  • [12] Friedel-Crafts Reaction of Benzyl Fluorides: Selective Activation of C-F Bonds as Enabled by Hydrogen Bonding
    Champagne, Pier Alexandre
    Benhassine, Yasmine
    Desroches, Justine
    Paquin, Jean-Francois
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (50) : 13835 - 13839
  • [13] UV Light Induced Direct Synthesis of Phenanthrene Derivatives from a Linear 3-Aryl-N-(arylsulfonyl) Propiolamides
    Chen, Ming
    Yang, Chao
    Wang, Yanpei
    Li, Dazhi
    Xia, Wujiong
    [J]. ORGANIC LETTERS, 2016, 18 (09) : 2280 - 2283
  • [14] Regiocontrolled Synthesis of Ethene-Bridged para-Phenylene Oligomers Based on PtII- and RuII-Catalyzed Aromatization
    Chen, Tse-An
    Lee, Te-Ju
    Lin, Ming-Yuan
    Sohel, Shariar M. A.
    Dian, Eric Wei-Guang
    Lush, Shie-Fu
    Liu, Rai-Shung
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (06) : 1826 - 1833
  • [15] Synthesis of (13C6-Ring-(U))-(±)-benzo(a)pyrene metabolites from (13C6-Ring-(U))benzene
    Diel, Bruce N.
    Han, Mingcheng
    Kole, Panna L.
    Boaz, David B.
    [J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2007, 50 (5-6) : 551 - 553
  • [16] Fluoroalcohols: versatile solvents in hypervalent iodine chemistry and syntheses of diaryliodonium(III) salts
    Dohi, Toshifumi
    Yamaoka, Nobutaka
    Kita, Yasuyuki
    [J]. TETRAHEDRON, 2010, 66 (31) : 5775 - 5785
  • [17] Fuchibe K., 2013, ANGEW CHEM, V125, P7979
  • [18] Pinpoint-fluorinated phenanthrene synthesis based on C-F bond activation of difluoroalkenes
    Fuchibe, Kohei
    Morikawa, Toshiyuki
    Ueda, Ryu
    Okauchi, Tatsuo
    Ichikawa, Junji
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2015, 179 : 106 - 115
  • [19] Pinpoint-Fluorinated Phenacenes: New Synthesis and Solubility Enhancement Strategies
    Fuchibe, Kohei
    Morikawa, Toshiyuki
    Shigeno, Kento
    Fujita, Takeshi
    Ichikawa, Junji
    [J]. ORGANIC LETTERS, 2015, 17 (05) : 1126 - 1129
  • [20] Domino Synthesis of Fluorine-Substituted Polycyclic Aromatic Hydrocarbons: 1,1-Difluoroallenes as Synthetic Platforms
    Fuchibe, Kohei
    Mayumi, Yuka
    Zhao, Nan
    Watanabe, Shumpei
    Yokota, Misaki
    Ichikawa, Junji
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (30) : 7825 - 7828
1234567