Synthesis of thioethers via metal-free reductive coupling of tosylhydrazones with thiols

被引:91
|
作者
Ding, Qiuping [1 ,2 ]
Cao, Banpeng [1 ]
Yuan, Jianjun [1 ]
Liu, Xianjin [1 ]
Peng, Yiyuan [1 ,2 ]
机构
[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Peoples R China
[2] Key Lab Green Chem Jiangxi Prov, Nanchang 330022, Peoples R China
关键词
ALPHA-DIAZOCARBONYL COMPOUNDS; BOND FORMATION; EFFICIENT SYNTHESIS; ADDITION-REACTIONS; ARYL HALIDES; H BONDS; SULFIDES; SELENIDES; CATALYST; ALKYL;
D O I
10.1039/c0ob00639d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A metal-free procedure for the synthesis of thioethers is described via the base-promoted reductive coupling of tosylhydrazones with thiols through an insertion of a carbene into the S-H bond.
引用
收藏
页码:748 / 751
页数:4
相关论文
共 50 条
  • [1] N-Alkylation of tosylhydrazones via a metal-free reductive coupling procedure
    Liu, Jin-Biao
    Yan, Hui
    Lu, Gui
    TETRAHEDRON LETTERS, 2013, 54 (08) : 891 - 895
  • [2] Synthesis of sulfur-containing polymers via metal-free cross coupling polymerization of tosylhydrazones and thiols
    Gao, Xin
    Song, Zeli
    Hu, Jianfeng
    Zhang, Hao
    POLYMER, 2022, 248
  • [3] Synthesis of sulfur-containing polymers via metal-free cross coupling polymerization of tosylhydrazones and thiols
    Gao, Xin
    Song, Zeli
    Hu, Jianfeng
    Zhang, Hao
    Polymer, 2022, 248
  • [4] Straightforward Synthesis of Ethers: Metal-Free Reductive Coupling of Tosylhydrazones with Alcohols or Phenols
    Barluenga, Jose
    Tomas-Gamasa, Maria
    Aznar, Fernando
    Valdes, Carlos
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (29) : 4993 - 4996
  • [5] Metal-free Reductive Coupling of Biphenyl Tosylhydrazones with Phenols or Benzyl Alcohols
    Liu, Yang
    Liu, Ping
    Liu, Yan
    Wei, Yu
    Dai, Bin
    LETTERS IN ORGANIC CHEMISTRY, 2017, 14 (10) : 748 - 757
  • [6] Synthesis of Densely Substituted Conjugated Dienes by Transition Metal-Free Reductive Coupling of Allenylboronic Acids and Tosylhydrazones
    Wang, Dong
    de Wit, Martin J. M.
    Szabo, Kalman J.
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (15): : 8786 - 8792
  • [7] A simple and efficient synthesis of 9-arylfluorenes via metal-free reductive coupling of arylboronic acids and N-tosylhydrazones in situ
    Shen, Xu
    Gu, Ningning
    Liu, Ping
    Ma, Xiaowei
    Xie, Jianwei
    Liu, Yan
    He, Lin
    Dai, Bin
    RSC ADVANCES, 2015, 5 (78) : 63726 - 63731
  • [8] Metal free coupling of heteroaryl N-tosylhydrazones and thiols: Efficient synthesis of sulfides
    Alfredo Garcia-Carrillo, Mario
    Guzman, Angel
    Diaz, Eduardo
    TETRAHEDRON LETTERS, 2017, 58 (20) : 1952 - 1956
  • [9] A Short Synthesis of (-)-6,7-Secoagroclavine via Metal-Free Reductive Coupling
    Diotallevi, Francesca
    Bartoccini, Francesca
    Piersanti, Giovanni
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (13)
  • [10] A metal-free desulfurizing radical reductive C-C coupling of thiols and alkenes
    Qin, Qixue
    Wang, Weijing
    Zhang, Cheng
    Song, Song
    Jiao, Ning
    CHEMICAL COMMUNICATIONS, 2019, 55 (71) : 10583 - 10586