Iodine-Mediated Cross-Dehydrogenative Coupling of Heterocyclic Thiols with Amines: An Easy and Practical Formation of S-N Bond

被引：9
作者：
Wu, Yue-Xiao [1 ]
Peng, Kang [1 ]
Hu, Zhi-Chao [1 ]
Fan, Yong-Hao [1 ]
Shi, Zhen [2 ]
Hao, Er-Jun [3 ]
Dong, Zhi-Bing [1 ,2 ,3 ,4 ,5 ]
机构：
[1] Wuhan Inst Technol, Sch Chem & Environm Engn, Wuhan 430205, Peoples R China
[2] Hubei Minzu Univ, Hubei Key Lab Biol Resources Protect & Utilizat, Enshi 445000, Peoples R China
[3] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China
[4] Wuhan Inst Technol, Key Lab Green Chem Proc, Minist Educ, Wuhan 430205, Peoples R China
[5] Wuhan Inst Technol, Hubei Key Lab Novel Reactor & Green Chem Technol, Wuhan 430205, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 2021卷 / 43期
关键词：
Cross-dehydrogenative coupling; Metal-free; S-N bond; Sulfenamide; Synthesis; CHEMISTRY; SULFENAMIDES; DISULFIDES; MOLECULES;
D O I：
10.1002/ejoc.202101165
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient iodine-mediated construction of S-N bond was developed. Such a cross-dehydrogenative coupling of heterocyclic thiols with amines proceeded smoothly under metal-free and base-free conditions, and afforded a series of sulfenamides in good to excellent yields. The easily available substrates and convenient synthetic procedure illustrate potential synthetic value of this protocol for the preparation of sulfenamide related biologically or pharmaceutically active compounds.
引用
收藏
页码：5889 / 5894
页数：6
相关论文
共 38 条
  • [1] Synthesis of Sulfinamidines and Sulfinimidate Esters by Transfer of Nitrogen to Sulfenamides
    Andresini, Michael
    Spennacchio, Mauro
    Romanazzi, Giuseppe
    Ciriaco, Fulvio
    Clarkson, Guy
    Degennaro, Leonardo
    Luisi, Renzo
    [J]. ORGANIC LETTERS, 2020, 22 (18) : 7129 - 7134
  • [2] [Anonymous], 2020, ANGEW CHEM, V132, P14347
  • [3] [Anonymous], 2019, ANGEW CHEM, V131, P14441
  • [4] Iodine Catalysis for C(sp3)-H Fluorination with a Nucleophilic Fluorine Source
    Bafaluy, Daniel
    Georgieva, Zoritsa
    Muniz, Kilian
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (34) : 14241 - 14245
  • [5] Origin of the Catalytic Effects of Molecular Iodine: A Computational Analysis
    Breugst, Martin
    Detmar, Eric
    von der Heiden, Daniel
    [J]. ACS CATALYSIS, 2016, 6 (05): : 3203 - 3212
  • [6] Synthesis of Sulfonimidamides from Sulfenamides via an Alkoxy-amino-λ6-sulfanenitrile Intermediate
    Briggs, Edward L.
    Tota, Arianna
    Colella, Marco
    Degennaro, Leonardo
    Luisi, Renzo
    Bull, James A.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (40) : 14303 - 14310
  • [7] Influence of sulfenamide accelerators on cure kinetics and properties of natural rubber foam
    Charoeythornkhajhornchai, Pollawat
    Samthong, Chavakorn
    Somwangthanaroj, Anongnat
    [J]. JOURNAL OF APPLIED POLYMER SCIENCE, 2017, 134 (19)
  • [8] THE CHEMISTRY OF SULFENAMIDES
    CRAINE, L
    RABAN, M
    [J]. CHEMICAL REVIEWS, 1989, 89 (04) : 689 - 712
  • [9] CHEMISTRY OF SULFUR-NITROGEN BOND .12. METAL-ASSISTED SYNTHESIS OF SULFENAMIDE DERIVATIVES FROM ALIPHATIC AND AROMATIC DISULFIDES
    DAVIS, FA
    FRIEDMAN, AJ
    KLUGER, EW
    SKIBO, EB
    FRETZ, ER
    MILICIA, AP
    LEMASTERS, WC
    BENTLEY, MD
    LACADIE, JA
    DOUGLASS, IB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (06) : 967 - 972
  • [10] Synthesis of Functionalized Diaryl Sulfides by Cobalt-Catalyzed Coupling between Arylzinc Pivalates and Diaryl Disulfides
    Dong, Zhi-Bing
    Balkenhohl, Moritz
    Tan, Eric
    Knochel, Paul
    [J]. ORGANIC LETTERS, 2018, 20 (23) : 7581 - 7584
1234