Hydrogen-Bonding Catalysis: Mild and Highly Chemoselective Oxidation of Sulfides

被引:32
|
作者
Russo, Alessio [1 ]
Lattanzi, Alessandra [1 ]
机构
[1] Univ Salerno, Dipartimento Chim, I-84084 Fisciano, Italy
关键词
chemoselectivity; hydrogen bonds; oxidation; sulfoxides; thioureas; TERT-BUTYL HYDROPEROXIDE; ASYMMETRIC OXIDATION; METAL-FREE; CHIRAL SULFOXIDES; PEROXIDE; ACID; ORGANOCATALYSIS; CONVENIENT; NITROALKENES; EPOXIDATION;
D O I
10.1002/adsc.200900020
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
N,N'-Bis[3,5-bis(trifluoromethyl)phenyl]thiourea, employed at only 1 mol% loading, was found to be a very effective catalyst for the oxidation of sulfides with tert-butyl hydroperoxide (TBHP), affording the sulfoxides in high yield, excellent chemoselectivity, fairly good diastereoselectivity.
引用
收藏
页码:521 / 524
页数:4
相关论文
共 50 条
  • [1] Tetrazole amides as hydrogen-bonding donor catalysts in the chemoselective oxidation of sulphides and disulphides
    Secci, Francesco
    Arca, Massimiliano
    Frongia, Angelo
    Piras, Pier Paolo
    CATALYSIS SCIENCE & TECHNOLOGY, 2014, 4 (05) : 1407 - 1415
  • [2] Hydrogen-bonding catalysis of sulfonium salts
    Kaneko, Shiho
    Kumatabara, Yusuke
    Shimizu, Shoichi
    Maruoka, Keiji
    Shirakawa, Seiji
    CHEMICAL COMMUNICATIONS, 2017, 53 (01) : 119 - 122
  • [3] CHEMOSELECTIVE OXIDATION OF SULFIDES TO SULFONES WITH POTASSIUM HYDROGEN PERSULFATE
    TROST, BM
    CURRAN, DP
    TETRAHEDRON LETTERS, 1981, 22 (14) : 1287 - 1290
  • [4] Cooperative Hydrogen-Bonding Effects in Silanediol Catalysis
    Tran, Ngon T.
    Wilson, Sean O.
    Franz, Annaliese K.
    ORGANIC LETTERS, 2012, 14 (01) : 186 - 189
  • [5] Cooperative photoredox and chiral hydrogen-bonding catalysis
    Yin, Yanli
    Zhao, Xiaowei
    Qiao, Baokun
    Jiang, Zhiyong
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (10) : 1283 - 1296
  • [6] Hydrogen-bonding in highly substituted pyrroles
    Baldwin, Charles M.
    Smith, Allorie T.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 69 - 69
  • [7] CHEMOSELECTIVE OXIDATION OF SULFIDES TO SULFONES WITH SELENIUM DIOXIDE HYDROGEN PEROXIDE
    KIM, KS
    HWANG, HJ
    HAHN, CS
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1989, 10 (05) : 482 - 483
  • [8] INTRAMOLECULAR HYDROGEN-BONDING CATALYSIS OF ESTER AMINOLYSIS IN ACETONITRILE
    CIUFFARIN, E
    LOI, A
    ISOLA, M
    LUPETTI, A
    SAGRAMORA, L
    SENATORE, L
    JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (07): : 1047 - 1051
  • [9] Hydrogen-bonding properties of organic silanols for asymmetric catalysis
    Franz, Annaliese K.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [10] HYDROGEN-BONDING IN ENZYMATIC CATALYSIS ANALYZED BY PROTEIN ENGINEERING
    WELLS, TNC
    FERSHT, AR
    NATURE, 1985, 316 (6029) : 656 - 657