Oxidative Trifluoromethylthiolation of Terminal Alkynes with AgSCF3: A Convenient Approach to Alkynyl Trifluoromethyl Sulfides

被引:55
|
作者
Zhu, Sheng-Qing [1 ]
Xu, Xiu-Hua [1 ]
Qing, Feng-Ling [1 ,2 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
[2] Donghua Univ, Coll Chem Chem Engn & Biotechnol, Shanghai 201620, Peoples R China
基金
中国国家自然科学基金;
关键词
Synthetic methods; Alkynes; Sulfur; Silver; Oxidation; ARYL BORONIC ACIDS; COPPER-CATALYZED TRIFLUOROMETHYLTHIOLATION; HYPERVALENT IODINE REAGENT; ALPHA-FLUORINATED ETHERS; NUCLEOPHILIC TRIFLUOROMETHYLTHIOLATION; ELECTROPHILIC TRIFLUOROMETHANESULFANYLATION; ENANTIOSELECTIVE TRIFLUOROMETHYLTHIOLATION; SUBSTITUENT CONSTANTS; DERIVATIVES; GENERATION;
D O I
10.1002/ejoc.201402533
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method for the efficient synthesis of alkynyl trifluoromethyl sulfides was developed. By combining AgSCF3 and NCS in N,N-dimethylacetamide, an electrophilic active intermediate was produced, which was then treated with a variety of terminal alkynes to afford the corresponding trifluoromethanesulfenylated products in moderate to excellent yields.
引用
收藏
页码:4453 / 4456
页数:4
相关论文
共 50 条
  • [1] Trifluoromethylthiolation of epoxides with AgSCF3: A new access to vinyl trifluoromethyl thioethers
    Chen, Hui-Ting
    Huang, Yangen
    Qing, Feng-Ling
    Xu, Xiu-Hua
    TETRAHEDRON LETTERS, 2020, 61 (12)
  • [2] Synthesis of 3-((trifluoromethyl)thio)indoles via trifluoromethylthiolation of 2-alkynyl azidoarenes with AgSCF3
    Phetcharawetch, Jongkonporn
    Betterley, Nolan M.
    Reutrakul, Vichai
    Soorukram, Darunee
    Leowanawat, Pawaret
    Kuhakarn, Chutima
    JOURNAL OF FLUORINE CHEMISTRY, 2021, 250
  • [3] Nucleophilic trifluoromethylthiolation of bromoalkynones with AgSCF3: C(sp)-SCF3 bond formation towards ynonyl trifluoromethyl sulfides
    Jiang, Huanfeng
    Zhu, Rui
    Zhu, Chuanle
    Chen, Fulin
    Wu, Wanqing
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (10) : 1646 - 1650
  • [4] Geometrically Selective Denitrative Trifluoromethylthiolation of β-Nitrostyrenes with AgSCF3 for (E)-Vinyl Trifluoromethyl Thioethers
    Zheng, Changge
    Huang, Shuai
    Liu, Yang
    Jiang, Chao
    Zhang, Wei
    Fang, Ge
    Hong, Jianquan
    ORGANIC LETTERS, 2020, 22 (12) : 4868 - 4872
  • [5] Direct copper-catalyzed oxidative trifluoromethylthiolation of aryl boronic acids with AgSCF3
    Wu, Wei
    Wang, Biyun
    Ji, Xinfei
    Cao, Song
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (07): : 1299 - 1303
  • [6] Copper(I)-promoted trifluoromethylthiolation of arenediazonium salts with AgSCF3
    Zheng, Changge
    Liu, Yang
    Hong, Jianquan
    Huang, Shuai
    Zhang, Wei
    Yang, Yupeng
    Fang, Ge
    TETRAHEDRON LETTERS, 2019, 60 (21) : 1404 - 1407
  • [7] Enantioselective α-Trifluoromethylthiolation of Carbonyl Compounds with AgSCF3 and Trichloroisocyanuric Acid
    Wang, Yakun
    Wang, Yingying
    Guo, Wenwen
    Zhang, Yizhe
    Du, Xiaoyu
    Song, Yan
    Wang, Wenhui
    Liu, Zhiang
    Duan, Yingchao
    Zhang, Tao
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (11): : 8011 - 8022
  • [8] Copper-mediated Trifluoromethylthiolation of Alkenyl Iodides with AgSCF3
    Kojima, Yuki
    Hirano, Koji
    CHEMISTRY LETTERS, 2023, 52 (10) : 791 - 793
  • [9] 1,2-Bis(trifluoromethylthiolation) of Aromatic Epoxides with AgSCF3
    Liu, Yin-Li
    Qing, Feng-Ling
    Xu, Xiu-Hua
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (08) : 1015 - 1018
  • [10] Copper-Assisted Oxidative Trifluoromethylthiolation of 2,3-Allenoic Acids with AgSCF3
    Pan, Shen
    Huang, Yangen
    Xu, Xiu-Hua
    Qing, Feng-Ling
    ORGANIC LETTERS, 2017, 19 (17) : 4624 - 4627