Controlled couplings of quinone monoacetals using reusable polystyrene-anchored specific proton catalyst

被引:16
作者
Dohi, Toshifumi [1 ]
Hu, Yinjun [1 ]
Kamitanaka, Tohru [1 ]
Kita, Yasuyuki [1 ]
机构
[1] Ritsumeikan Univ, Coll Pharmaceut Sci, Shiga 5258577, Japan
关键词
Bronsted acid; Heterogeneous catalysis; Recycling; Quinones; Heterocyclic compd; Fluoroalcohol; HYPERVALENT IODINE REAGENTS; CONJUGATE ADDITIONS; GRIGNARD-REAGENTS; CHEMISTRY; MONOKETALS; AMINOMETHYL; RESIN; OLIGOMERIZATION; CYCLOADDITION; AROMATIZATION;
D O I
10.1016/j.tet.2012.07.089
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Controlled couplings of quinone monoacetals 1 with soft nucelophiles have been achieved using a new and reusable perfluorobenzoic acid (PFBA) immobilized on polystyrene beads as an efficient polymer-anchored specific proton. Various advantages regarding the recovery, reusability, and reproducibility as well as the high chemoselectivity toward quinone monoacetals 1 have been determined as the key features of the cleaner systems with newly developed solid acid promoter for the reactions. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8424 / 8430
页数:7
相关论文
共 70 条
  • [1] A reinvestigation of the preparation, properties, and applications of aminomethyl and 4-methylbenzhydrylamine polystyrene resins
    Adams, JH
    Cook, RM
    Hudson, D
    Jammalamadaka, V
    Lyttle, MH
    Songster, MF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (11) : 3706 - 3716
  • [2] Methods and Protocols of modern solid phase peptide synthesis
    Amblard, M
    Fehrentz, JA
    Martinez, J
    Subra, G
    [J]. MOLECULAR BIOTECHNOLOGY, 2006, 33 (03) : 239 - 254
  • [3] The Diels-Alder reactions of quinone imine ketals
    Banfield, SC
    Kerr, MA
    [J]. CANADIAN JOURNAL OF CHEMISTRY, 2004, 82 (02) : 131 - 138
  • [4] Barany G., 1980, PEPTIDES, V2, P1
  • [5] Fluorinated alcohols:: A new medium for selective and clean reaction
    Bégué, JP
    Bonnet-Delpon, D
    Crousse, B
    [J]. SYNLETT, 2004, (01) : 18 - 29
  • [6] Polymer-supported organic catalysts
    Benaglia, M
    Puglisi, A
    Cozzi, F
    [J]. CHEMICAL REVIEWS, 2003, 103 (09) : 3401 - 3429
  • [7] Intriguing formal [2+3] cycloaddition promoted by a hypervalent iodine reagent
    Berard, Didier
    Giroux, Marc-Andre
    Racicot, Leanne
    Sabot, Cyrille
    Canesi, Sylvain
    [J]. TETRAHEDRON, 2008, 64 (32) : 7537 - 7544
  • [8] Traceless solid-phase organic synthesis
    Blaney, P
    Grigg, R
    Sridharan, V
    [J]. CHEMICAL REVIEWS, 2002, 102 (07) : 2607 - 2624
  • [9] Brown RCD, 1998, J CHEM SOC PERK T 1, P3293
  • [10] Synthesis of polysubstituted bicyclo[3.3.1]nonane-3,7-diones from cyclohexa-2,5-dienones and dimethyl 1,3-acetonedicarboxylate
    Camps, P
    González, A
    Muñoz-Torrero, D
    Simon, M
    Zúñiga, A
    Martins, MA
    Font-Bardia, M
    Solans, X
    [J]. TETRAHEDRON, 2000, 56 (41) : 8141 - 8151