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
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 50 条
  • [41] Visible-light-induced iron-catalyzed S-N cross-coupling of thiols with dioxazolones
    Tang, Jing-Jing
    Yan, Ning
    Zhang, Yiwei
    Wang, Yi
    Bao, Ming
    Yu, Xiaoqiang
    GREEN CHEMISTRY, 2023, 25 (19) : 7529 - 7533
  • [42] Synthesis of Polycyclic Amines through Mild Metal-Free Tandem Cross-Dehydrogenative Coupling/Intramolecular Hydroarylation of N-Aryltetrahydroisoquinolines and Crotonaldehyde
    Wu, Xiang
    Chen, Dian-Feng
    Chen, Shu-Sen
    Zhu, Yi-Fan
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (03) : 468 - 473
  • [43] Efficient visible light-mediated cross-dehydrogenative coupling reactions of tertiary amines catalyzed by a polymer-immobilized iridium-based photocatalyst
    Yoo, Woo-Jin
    Kobayashi, Shu
    GREEN CHEMISTRY, 2014, 16 (05) : 2438 - 2442
  • [44] Formation of C-O Bond via Cross-Dehydrogenative Coupling between Isochroman and Oxime under Metal-Free Oxidation Conditions
    He, Hua-Feng
    Wang, Kai
    Xing, Bo
    Sheng, Guorong
    Ma, Tingxuan
    Bao, Weiliang
    SYNLETT, 2013, 24 (02) : 211 - 214
  • [45] Iodine-Mediated Intramolecular Dehydrogenative Coupling: Synthesis of N-Alkylindolo[3,2-c]- and -[2,3-c]quinoline Iodides
    Volvoikar, Prajesh S.
    Tilve, Santosh G.
    ORGANIC LETTERS, 2016, 18 (05) : 892 - 895
  • [46] An Efficient and Practical Construction of S-N Bond from Aryl Thioureas and Amines under Metal-Free Conditions
    Hu, Zhi-Chao
    Wu, Yue-Xiao
    Ye, Lei
    Cui, Jing-Jing
    Dong, Zhi-Bing
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (29)
  • [47] Bu4NI Catalyzed C-N Bond Formation via Cross-Dehydrogenative Coupling of Aryl Ethers (Csp3-H) and Tetrazoles (N-H)
    Rajamanickam, Suresh
    Majji, Ganesh
    Santra, Sourav Kumar
    Patel, Bhisma K.
    ORGANIC LETTERS, 2015, 17 (22) : 5586 - 5589
  • [48] N-Mannich Bases of Aromatic Heterocyclic Amides: Synthesis via Copper-Catalyzed Aerobic Cross-Dehydrogenative Coupling under Ambient Conditions
    Singh, Shailendra K.
    Chandna, Nisha
    Jain, Nidhi
    ORGANIC LETTERS, 2017, 19 (06) : 1322 - 1325
  • [49] Iodine catalyzed solvent-free cross-dehydrogenative coupling of arylamines and H-phosphonates for the synthesis of N-arylphosphoramidates under atmospheric conditions
    Dar, Bashir Ahmad
    Dangroo, Nisar A.
    Gupta, Amit
    Wali, Aarti
    Khuroo, Mohammad Akbar
    Vishwakarma, Ram A.
    Singh, Baldev
    TETRAHEDRON LETTERS, 2014, 55 (09) : 1544 - 1548
  • [50] TEMPO-Catalyzed Aerobic Oxidative Coupling of Thiols for Metal-Free Formation of S-N/S-S Bonds
    Yang, Liting
    Li, Shuding
    Dou, Yingchao
    Zhen, Shan
    Li, Heng
    Zhang, Panke
    Yuan, Bingxin
    Yang, Guanyu
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (03) : 265 - 268