Radical Aromatic Trifluoromethylthiolation: Photoredox Catalysis vs. Base Mediation

被引：30
作者：
Koziakov, Denis [1 ]
Majek, Michal [1 ]
Jacobi von Wangelin, Axel [1 ,2 ]
机构：
[1] Univ Regensburg, Inst Organ Chem, Regensburg, Germany
[2] Univ Hamburg, Dept Chem, Martin Luther King Pl 6, D-20146 Hamburg, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 45期
关键词：
Aromatic substitution; Photoredox catalysis; Radical reactions; Fluorinations; Thiols; Fluorine; ARYL FLUOROALKYL SULFIDES; OXIDATIVE TRIFLUOROMETHYLTHIOLATION; NUCLEOPHILIC TRIFLUOROMETHYLATION; SELECTIVE FLUORINATION; CONVENIENT SYNTHESIS; LIQUID-CRYSTALS; DRUG DESIGN; CHEMISTRY; PERFLUOROALKYLATION; HALOGENOPERFLUOROALKANES;
D O I：
10.1002/ejoc.201701339
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Trifluoromethyl aryl sulfides (Ar-SCF3) constitute highly attractive building blocks due to their exceptional lipophilicity and chemical properties. Related protocols of radical aromatic trifluoro-methylthiolation of arenediazonium salts were developed that are based on the facile generation of intermediate aryl radicals. Their reactions with commercial F3CS-SCF3 under very mild conditions afforded a diverse set of Ar-SCF3 (< 90% yield). Direct comparison of photoredox catalysis {eosin Y or [Ru(bpy)(3)]Cl-2} with the weak base-mediated dark reaction documented higher synthetic efficiency of the former but higher operational simplicity of the latter strategy.
引用
收藏
页码：6722 / 6725
页数：4
相关论文
共 90 条
  • [1] Trifluoromethylthiodediazoniation: a simple, efficient route to trifluoromethyl aryl sulfides
    Adams, DJ
    Goddard, A
    Clark, JH
    Macquarrie, DJ
    [J]. CHEMICAL COMMUNICATIONS, 2000, (11) : 987 - 988
  • [2] ANDRE JN, 1979, BRIT J PHARMACOL, V66, pP506
  • [3] ARYL FLUOROALKYL SULFIDES .2. PREPARATION BY CONDENSATION OF TRIFLUOROMETHANESULFENYL CHLORIDE WITH AROMATIC SYSTEMS
    ANDREADES, S
    SHEPPARD, WA
    HARRIS, JF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (04) : 898 - &
  • [4] [Anonymous], 2013, Angew. Chem, DOI [10.1002/ange.201209817, DOI 10.1002/ANGE.201209817]
  • [5] [Anonymous], 2011, Angew. Chem., DOI [10.1002/ange.201102543, DOI 10.1002/ANGE.201102543]
  • [6] [Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1002/ANGE.201205156
  • [7] [Anonymous], 2013, ANGEW CHEM, DOI [10.1002/ange.201208432, DOI 10.1002/ANGE.201208432]
  • [8] Anton D, 1998, ADV MATER, V10, P1197, DOI 10.1002/(SICI)1521-4095(199810)10:15<1197::AID-ADMA1197>3.0.CO
  • [9] 2-F
  • [10] Fluorinated organic materials for electronic and optoelectronic applications: the role of the fluorine atom
    Babudri, Francesco
    Farinola, Gianluca M.
    Naso, Francesco
    Ragni, Roberta
    [J]. CHEMICAL COMMUNICATIONS, 2007, (10) : 1003 - 1022
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