Hydrogen-bonding catalysis of sulfonium salts

被引:37
作者
Kaneko, Shiho [1 ]
Kumatabara, Yusuke [1 ]
Shimizu, Shoichi [2 ]
Maruoka, Keiji [3 ]
Shirakawa, Seiji [1 ]
机构
[1] Nagasaki Univ, Grad Sch Fisheries & Environm Sci, Dept Environm Sci, 1-14 Bunkyo Machi, Nagasaki 8528521, Japan
[2] Nihon Univ, Coll Ind Technol, Dept Appl Mol Chem, Izumi Cho, Narashino, Chiba 2758575, Japan
[3] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
关键词
QUATERNARY PHOSPHONIUM SALTS; DIRECT REDUCTIVE AMINATION; PHASE-TRANSFER CATALYSTS; ANION-BINDING CATALYSIS; DIELS-ALDER REACTION; ENANTIOSELECTIVE SYNTHESIS; TETRAALKYLAMMONIUM SALTS; DANISHEFSKYS DIENE; CARBONYL-COMPOUNDS; ORGANOCATALYSIS;
D O I
10.1039/c6cc08411g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Although quaternary ammonium and phosphonium salts are known as important catalysts in phase-transfer catalysis, the catalytic ability of tertiary sulfonium salts has not yet been well demonstrated. Herein, we demonstrate the catalytic ability of trialkylsulfonium salts as hydrogenbonding catalysts on the basis of the characteristic properties of the acidic a hydrogen atoms on alkylsulfonium salts.
引用
收藏
页码:119 / 122
页数:4
相关论文
共 82 条
  • [1] Design Strategies for Enhanced Hydrogen- Bond Donor Catalysts
    Auvil, Tyler J.
    Schafer, Andrew G.
    Mattson, Anita E.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (13) : 2633 - 2646
  • [2] Molecular iodine catalyzed transfer hydrogenation: reduction of aldimines, ketimines, and α-imino esters
    Bachu, Prabhakar
    Zhu, Chen
    Akiyama, Takahiko
    [J]. TETRAHEDRON LETTERS, 2013, 54 (30) : 3977 - 3981
  • [3] Anion-Binding Catalysis by Electron-Deficient Pyridinium Cations
    Berkessel, Albrecht
    Das, Somnath
    Pekel, Daniel
    Neudoerfl, Joerg-M.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (43) : 11660 - 11664
  • [4] Magnitudes and chemical consequences of R3N+-C-H•••O=C hydrogen bonding
    Cannizzaro, CE
    Houk, KN
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (24) : 7163 - 7169
  • [5] Radical substituent effects of α-sulfonium groups
    Cheng, JP
    Liu, B
    Zhang, XM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) : 7574 - 7575
  • [6] Quantum Mechanical Transition-State Analysis Reveals the Precise Origin of Stereoselectivity in Chiral Quaternary Cinchonidinium Phase-Transfer Catalyzed Enolate Allylation
    Cook, Thomas C.
    Andrus, Merritt B.
    Ess, Daniel H.
    [J]. ORGANIC LETTERS, 2012, 14 (23) : 5836 - 5839
  • [7] Dehmlow E.V., 1993, PHASE TRANSFER CATAL
  • [8] Small-molecule H-bond donors in asymmetric catalysis
    Doyle, Abigail G.
    Jacobsen, Eric N.
    [J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5713 - 5743
  • [9] Chiral quaternary phosphonium salts: a new class of organocatalysts
    Enders, Dieter
    Thanh Vinh Nguyen
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (28) : 5327 - 5331
  • [10] CRYSTAL AND MOLECULAR-STRUCTURE OF 1-METHYL-1-THIONIA-CYCLOHEXANE IODIDE
    GERDIL, R
    [J]. HELVETICA CHIMICA ACTA, 1974, 57 (02) : 489 - 493