Rapid synthesis of aryl sulfides through metal-free C-S coupling of thioalcohols with diaryliodonium salts

被引：15
|
作者：
Wang, Dawei [1 ]
Yu, Xin [1 ]
Zhao, Keyan [1 ]
Li, Liang [1 ]
Ding, Yuqiang [1 ]
机构：
[1] Jiangnan Univ, Sch Chem & Mat Engn, Key Lab Food Colloids & Biotechnol, Minist Educ, Wuxi 214122, Jiangsu, Peoples R China
来源：
TETRAHEDRON LETTERS | 2014年 / 55卷 / 42期
基金：
中国国家自然科学基金;
关键词：
C-S coupling; Metal free; Diaryliodonium; Rapid; Chemoselectivity; EFFICIENT SYNTHESIS; FACILE SYNTHESIS; ALPHA-ARYLATION; COPPER; PALLADIUM; LIGAND; THIOLS; CATALYST; IODIDES; HALIDES;
D O I：
10.1016/j.tetlet.2014.08.088
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient, general, and highly selective method for the synthesis of aryl sulfides has been developed through metal-free, direct C-S coupling from thioalcohols and diaryliodonium salts. Significantly, the reaction took only 10 min to complete and produced high yields at room temperature. Thus, this methodology proves its value as a versatile synthetic choice for a broad range of aryl sulfides, producing good to excellent yields. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5739 / 5741
页数：3
相关论文
共 50 条
  • [31] Metal-Free C-S Bond Formation in Elemental Sulfur and Cyclobutanol Derivatives: The Synthesis of Substituted Thiophenes
    Wu, Mingzhong
    Yan, Chaoxian
    Zhuang, Daijiao
    Yan, Rulong
    [J]. ORGANIC LETTERS, 2022, 24 (29) : 5309 - 5313
  • [32] Metal-Free and Open-Air Arylation Reactions of Diaryliodonium Salts for DNA-Encoded Library Synthesis
    Xu, Hongtao
    Tan, Tingting
    Zhang, Yiyuan
    Wang, Yan
    Pan, Kangyin
    Yao, Ying
    Zhang, Shuning
    Gu, Yuang
    Chen, Wanting
    Li, Jie
    Dong, Hewei
    Meng, Yu
    Ma, Peixiang
    Hou, Wei
    Yang, Guang
    [J]. ADVANCED SCIENCE, 2022, 9 (26)
  • [33] Metal-Free Synthesis of Phenol-Aryl Selenides via Dehydrogenative C-Se Coupling of Aryl Selenoxides with Phenols
    Liu, Zhengfen
    Jiang, Yonggang
    Liu, Chunxiang
    Zhang, Linlin
    Wang, Jing
    Li, Tiantian
    Zhang, Hongbin
    Li, Minyan
    Yang, Xiaodong
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (11): : 7386 - 7398
  • [34] Metal-Free Visible-light Mediated C-S Bond Formation
    Sahoo, Ashish Kumar
    Barik, Dinabandhu
    Dam, Binoyargha
    Patel, Bhisma K.
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (08)
  • [35] Green Synthesis of Aryl Thioethers through Cu-catalysed C-S Coupling of Thiols and Aryl Boronic Acids in Water
    Tu Peihua
    Jiang Jun
    Xiao Hongping
    Li Xinhua
    [J]. JOURNAL OF WUHAN UNIVERSITY OF TECHNOLOGY-MATERIALS SCIENCE EDITION, 2019, 34 (04): : 987 - 993
  • [36] Green Synthesis of Aryl Thioethers through Cu-catalysed C-S Coupling of Thiols and Aryl Boronic Acids in Water
    Peihua Tu
    Jun Jiang
    Hongping Xiao
    Xinhua Li
    [J]. Journal of Wuhan University of Technology-Mater. Sci. Ed., 2019, 34 : 987 - 993
  • [37] Green Synthesis of Aryl Thioethers through Cu-catalysed C-S Coupling of Thiols and Aryl Boronic Acids in Water
    涂佩华
    JIANG Jun
    XIAO Hongping
    李新华
    [J]. Journal of Wuhan University of Technology(Materials Science), 2019, 34 (04) : 987 - 993
  • [38] Palladium(II)-mediated 11C-carbonylative coupling of diaryliodonium salts with organostannanes -: a new, mild and rapid synthesis of aryl [11C]ketones
    Al-Qahtani, MH
    Pike, VW
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (06): : 1033 - 1036
  • [39] Metal-free S-arylation of 5-mercaptotetrazoles and 2-mercaptopyridine with unsymmetrical diaryliodonium salts
    Saikia, Raktim Abha
    Hazarika, Nitumoni
    Biswakarma, Nishant
    Deka, Ramesh Chandra
    Thakur, Ashim Jyoti
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (19) : 3890 - 3896
  • [40] Transition metal-free coupling reactions of benzylic trimethylammonium salts with di(hetero)aryl disulfides and diselenides
    Li, Fuhai
    Wang, Dan
    Chen, Hongyi
    He, Ze
    Zhou, Lihong
    Zeng, Qingle
    [J]. CHEMICAL COMMUNICATIONS, 2020, 56 (85) : 13029 - 13032
12345