Direct Phosphorus-Induced Fluoroalkylthiolation with Fluoroalkylsulfonyl Chlorides

被引:67
作者
Jiang, Lvqi [1 ]
Yi, Wenbin [1 ]
Liu, Qiran [1 ]
机构
[1] Nanjing Univ Sci & Technol, Chem Engn Coll, 200 Xiao Ling Wei St, Nanjing, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
electron-rich arenes and thiols; fluoroalkylsulfonyl chlorides; fluoroalkylthiolation; phosphorus-induced reaction; HYPERVALENT IODINE REAGENT; ELECTROPHILIC TRIFLUOROMETHYLTHIOLATION; ANTIARRHYTHMICS; FLUORINATION; SULFIDES; EFFICACY; INDOLES; ALKENES; BONDS; ARYL;
D O I
10.1002/adsc.201600651
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A simple and practical method of fluoroalkylthiolation using fluoroalkylsulfonyl chlorides (RfSO2Cl, R-f=CF3, C4F9, C8F17, CF2H and CH2CF3) has been developed. These easy-to-handle reagents are powerful and can be used for electrophilic fluoroalkylthiolation of electron-rich arenes and thiols using diethyl phosphite as reducing agent.
引用
收藏
页码:3700 / 3705
页数:6
相关论文
共 73 条
  • [1] Alazet S., 2013, ANGEW CHEM, V125, P11014, DOI DOI 10.1002/ANGE.201305179
  • [2] Electrophilic Trifluoromethylthiolation of Carbonyl Compounds
    Alazet, Sebastien
    Zimmer, Luc
    Billard, Thierry
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (28) : 8589 - 8593
  • [3] Base-Catalyzed Electrophilic Trifluoromethylthiolation of Terminal Alkynes
    Alazet, Sebastien
    Zimmer, Luc
    Billard, Thierry
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (41) : 10814 - 10817
  • [4] [Anonymous], 2013, ANGEW CHEM, DOI DOI 10.1002/ANGE.201301438
  • [5] [Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1002/ANGE.201205156
  • [6] [Anonymous], 2013, ANGEW CHEM, DOI [DOI 10.1002/ANGE.201206566, 10.1002/ange.201206566]
  • [7] [Anonymous], 2009, ANGEW CHEM
  • [8] Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis
    Arimori, Sadayuki
    Matsubara, Okiya
    Takada, Masahiro
    Shiro, Motoo
    Shibata, Norio
    [J]. ROYAL SOCIETY OPEN SCIENCE, 2016, 3 (05):
  • [9] Electrophilic Trifluoromethanesulfanylation of Organometallic Species with Trifluoromethanesulfanamides
    Baert, Francois
    Colomb, Julie
    Billard, Thierry
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (41) : 10382 - 10385
  • [10] ANTIARRHYTHMICS - N-(AMINOALKYLENE)TRIFLUOROETHOXYBENZAMIDES AND N-(AMINOALKYLENE)TRIFLUOROETHOXYNAPHTHAMIDES
    BANITT, EH
    COYNE, WE
    SCHMID, JR
    MENDEL, A
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1975, 18 (11) : 1130 - 1134