Electrophilic Aromatic Trifluoromethylthiolation with the Second Generation of Trifluoromethanesulfenamide

被引:52
作者
Alazet, Sebastien [1 ,2 ]
Billard, Thierry [1 ,2 ]
机构
[1] Univ Lyon 1, CNRS, Univ Lyon, Inst Chem & Biochem,ICBMS,UMR 5246, F-69622 Lyon, France
[2] Groupement Hospitalier Est, CERMEP, F-69003 Lyon, France
关键词
trifluoromethylthiolation; fluorine; arenes; heterocycles; trifluoromethanesulfenamide; MEDICINAL CHEMISTRY; FLUORINE; PREDICTION;
D O I
10.1055/s-0034-1379501
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Direct trifluoromethylthiolation of various aromatic and heteroaromatic compounds, variously substituted, can be performed with the second generation of trifluoromethanesulfenamide via a 'Friedel-Crafts-like reaction'. This reaction requires mild conditions with a catalytic amount of protic or Lewis acid. Good results have been obtained, even with aromatic compounds bearing deactivating substituents.
引用
收藏
页码:76 / 78
页数:3
相关论文
共 50 条
  • [31] Deoxygenative 1,1-Bis-trifluoromethylthiolation of Aromatic Aldehydes to Access Bis(trifluoromethylthio)methylarenes
    Liu, Yin-Li
    Xu, Xiu-Hua
    Qing, Feng-Ling
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (22) : 5031 - 5035
  • [32] Synthesis of α-Trifluoromethylthio-α,β-Unsaturated Carbonyl Compounds by DABCO-Mediated Electrophilic Trifluoromethylthiolation with N-SCF3-Dibenzenesulfonimide
    Yoo, Jeyeon
    Ha, Heun-Jong
    Kim, Bora
    Cho, Chang-Woo
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (11) : 7077 - 7085
  • [33] Electrophilic aromatic fluorination with fluorine:: meta-Directed fluorination of anilines
    Alric, JP
    Marquet, B
    Billard, T
    Langlois, BR
    JOURNAL OF FLUORINE CHEMISTRY, 2005, 126 (04) : 661 - 667
  • [34] Transition-metal- and phosphorus-free electrophilic trifluoromethylthiolation of indoles with sodium trifluoromethanesulfinates in ionic liquids
    Wang, Fei
    Lu, Guo-Ping
    Lin, Yamei
    TETRAHEDRON LETTERS, 2021, 70
  • [35] Electrophilic Trifluoromethylthiolation/Semipinacol Rearrangement: Preparation of β-SCF3 Carbonyl Compounds with α-Quaternary Carbon Center
    Xi, Chao-Chao
    Chen, Zhi-Min
    Zhang, Shu-Yu
    Tu, Yong-Qiang
    ORGANIC LETTERS, 2018, 20 (14) : 4227 - 4230
  • [36] An analysis of electrophilic aromatic substitution: a "complex approach"
    Stamenkovic, Nikola
    Ulrih, Natasa Poklar
    Cerkovnik, Janez
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2021, 23 (09) : 5051 - 5068
  • [37] The selectivity problem in electrophilic fluorination of aromatic compounds
    Borodkin, G. I.
    Shubin, V. G.
    RUSSIAN CHEMICAL REVIEWS, 2010, 79 (04) : 259 - 283
  • [38] Regioselective control of electrophilic aromatic substitution reactions
    Smith, K
    El-Hiti, GA
    CURRENT ORGANIC SYNTHESIS, 2004, 1 (03) : 253 - 274
  • [39] Electrophilic Difluoro(phenylthio)methylation: Generation, Stability, and Reactivity of α-Fluorocarbocations
    Betterley, Nolan M.
    Surawatanawong, Panida
    Prabpal, Samran
    Kongsaeree, Palangpon
    Kuhakarn, Chutima
    Pohmakotr, Manat
    Reutrakul, Vichai
    ORGANIC LETTERS, 2013, 15 (22) : 5666 - 5669
  • [40] Mechanism and Origins of Stereoinduction in Natural Cinchona Alkaloid Catalyzed Asymmetric Electrophilic Trifluoromethylthiolation of β-Keto Esters with N-Trifluoromethylthiophthalimide as Electrophilic SCF3 Source
    Li, Man
    Xue, Xiao-Song
    Cheng, Jin-Pei
    ACS CATALYSIS, 2017, 7 (11): : 7977 - 7986