TfOH-catalyzed three-component synthesis of Dithiocarbamates from a-Diazoesters under continuous flow conditions

被引:6
|
作者
Wang, Rui [1 ,2 ]
He, Hangli [1 ,2 ]
Yan, Qiongjiao [1 ]
Wang, Wei [1 ]
Wang, Haifeng [1 ,2 ]
Chen, Fener [1 ,3 ,4 ]
机构
[1] Wuhan Inst Technol, Pharmaceut Res Inst, Wuhan 430205, Peoples R China
[2] Wuhan Inst Technol, Sch Chem Engn & Pharm, Wuhan 430205, Peoples R China
[3] Fudan Univ, Engn Ctr Catalysis & Synth Chiral Mol, Dept Chem, Shanghai 200433, Peoples R China
[4] Shanghai Engn Ctr Ind Catalysis Chiral Drugs, Shanghai 200433, Peoples R China
关键词
Diazo compounds; Continuous flow; Dithiocarbamates; Acid catalyzed; Three-component reaction; DERIVATIVES; MECHANISM; INSERTION; ACCESS; WATER;
D O I
10.1007/s41981-022-00249-7
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis of dithiocarbamates derivatives is important for their practical utilization as pharmaceuticals and for other purposes. Herein, we demonstrated the TfOH-catalyzed synthesis of dithiocarbamates via three-component reaction of alpha-diazoesters in good yields under continuous flow conditions. The reaction exhibits a wide substrate scope of diazo compounds and high functional group tolerance. This study provides a safe and mild protocol to form dithiocarbamates that complements TfOH-catalyzed S-H insertion reaction of diazo compounds and continuous flow synthesis strategies.
引用
收藏
页码:1 / 8
页数:8
相关论文
共 50 条
  • [1] TfOH-catalyzed three-component synthesis of Dithiocarbamates from α-Diazoesters under continuous flow conditions
    Rui Wang
    Hangli He
    Qiongjiao Yan
    Wei Wang
    Haifeng Wang
    Fener Chen
    Journal of Flow Chemistry, 2023, 13 : 1 - 8
  • [2] Visible-Light-Induced Synthesis of Thioethers through Three-Component Reactions of a-Diazoesters, Thiols, and Cyclic Ethers
    Lv, Yufen
    Wang, Zhiwei
    Hao, Jindong
    Zhao, Xiaohui
    Wei, Wei
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (08)
  • [3] TfOH/C-catalyzed one-pot three-component synthesis of α-amino phosphonates under solvent-free conditions
    Abbas Ali Jafari
    Sakineh Amini
    Fatemeh Tamaddon
    Journal of the Iranian Chemical Society, 2013, 10 : 677 - 684
  • [4] TfOH/C-catalyzed one-pot three-component synthesis of α-amino phosphonates under solvent-free conditions
    Jafari, Abbas Ali
    Amini, Sakineh
    Tamaddon, Fatemeh
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2013, 10 (04) : 677 - 684
  • [5] TfOH-Catalyzed Regioselective Alkylation of Hydroxybenzotriazole with Diazo Compounds and Further Base-Facilitated Elimination under Batch and Flow Conditions
    Luo, Mengxiang
    Wang, Rui
    Li, Yang
    Gong, Jiahao
    Gu, Shuangxi
    Yan, Qiongjiao
    Lv, Jian
    Zeng, Jie
    Wang, Wei
    Wang, Haifeng
    Chen, Fener
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 13 (02)
  • [6] Convergent Synthesis of Dihydropyrans from Catalytic Three-Component Reactions of Vinylcyclopropanes, Diazoesters, and Diphenyl Sulfoxide
    Zhang, Ya-Lin
    Guo, Rui-Ting
    Luo, Heng
    Liang, Xin-Shen
    Wang, Xiao-Chen
    ORGANIC LETTERS, 2020, 22 (14) : 5627 - 5632
  • [7] A microwave-assisted, copper-catalyzed three-component synthesis of dihydropyrimidinones under mild conditions
    Pasunooti, Kalyan Kumar
    Chai, Hua
    Jensen, Chantel Nixon
    Gorityala, Bala Kishan
    Wang, Siming
    Liu, Xue-Wei
    TETRAHEDRON LETTERS, 2011, 52 (01) : 80 - 84
  • [8] A one-pot three-component synthesis of dithiocarbamates starting from vinyl pyridines and vinyl pyrazine under solvent- and catalyst-free conditions
    Halimehjani, Azim Ziyaei
    Martens, Juergen
    Schlueter, Torben
    TETRAHEDRON, 2016, 72 (27-28) : 3958 - 3965
  • [9] Chemoselective three-component synthesis of α-carbolines under metal-free conditions
    Feng, Wei
    Zhang, Chao
    Zhou, Xinlin
    You, Kuiyi
    Deng, Guo-Jun
    Chen, Shanping
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (21) : 5457 - 5462
  • [10] Three-Component Synthesis of α-Branched Amines under Barbier-like Conditions
    Le Gall, Erwan
    Haurena, Caroline
    Sengmany, Stephane
    Martens, Thierry
    Troupel, Michel
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (20): : 7970 - 7973