Catalyst-Free and Base-Free Water-Promoted SNAr Reaction of Heteroaryl Halides with Thiols

被引:38
|
作者
Sreedhar, B. [1 ]
Reddy, P. Surendra [1 ]
Reddy, M. Amarnath [1 ]
机构
[1] Indian Inst Chem Technol, Inorgan & Phys Chem Div, Hyderabad 500007, Andhra Pradesh, India
来源
SYNTHESIS-STUTTGART | 2009年 / 10期
关键词
heteroaryl halides; thiophenol; SNAr reaction; water; 2-thiopyridines; EFFICIENT SYNTHESIS; ARYL; EPOXIDES;
D O I
10.1055/s-0029-1216644
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and efficient route for the synthesis of biaryl sulfides have been developed in aqueous medium under base- and catalyst-free conditions. A wide variety of heteroaryl halides and thiols underwent SNAr reaction to provide diaryl sulfides in good to excellent yields. The remarkable key features of the reaction include the use of water as an inexpensive and environmentally benign reaction medium, absence of any additional reagent or catalyst, and easy isolation of the products.
引用
收藏
页码:1732 / 1738
页数:7
相关论文
共 50 条
  • [1] Ligand and base-free Heck reaction with heteroaryl halides
    Kantam, M. Lakshmi
    Reddy, P. Vishnuvardhan
    Srinivas, P.
    Bhargava, Suresh
    [J]. TETRAHEDRON LETTERS, 2011, 52 (34) : 4490 - 4493
  • [2] Water promoted catalyst-free anti-Markovnikov addition of thiols to styrenes
    Movassagh, Barahman
    Navidi, Mozhgan
    [J]. ARKIVOC, 2008, : 47 - 53
  • [3] Rapid microwave-promoted catalyst- and base-free Suzuki-type coupling reaction in water
    Yan, Jie
    Zhu, Min
    Zhou, Zhongshi
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (09) : 2060 - 2062
  • [4] Base-Free and Catalyst-Free Synthesis of Functionalized Dihydrobenzoxazoles via Vinylogous Carbonate to Carbamate Rearrangement
    Das, Tamal Kanti
    Mondal, Santigopal
    Gonnade, Rajesh G.
    Bije, Akkattu T.
    [J]. ORGANIC LETTERS, 2017, 19 (20) : 5597 - 5600
  • [5] Catalyst-Free Aldol Reaction in a Water Medium
    Yao, Weirong
    Cui, Yanli
    Wang, Peipei
    Mao, Yangyi
    [J]. LETTERS IN ORGANIC CHEMISTRY, 2016, 13 (04) : 293 - 296
  • [6] Catalyst-free, visible-light-promoted S-H insertion reaction between thiols and α-diazoesters
    Yang, Jingya
    Wang, Ganggang
    Chen, Shuwen
    Ma, Ben
    Zhou, Hongyan
    Song, Menghui
    Liu, Cai
    Huo, Congde
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (46) : 9494 - 9498
  • [7] Base-Free Cu(II)-Catalyzed Coupling Reaction of Arylboronic Acids and Thiols
    Yang, Minghua
    Pei, Ji
    Yan, Guobing
    Weng, Qiuyue
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2013, 33 (02) : 343 - 347
  • [8] Catalyst-free conjugated addition of thiols to α,β-unsaturated carbonyl compounds in water
    Khatik, Gopal L.
    Kumar, Raj
    Chakraborti, Asit K.
    [J]. ORGANIC LETTERS, 2006, 8 (11) : 2432 - 2436
  • [9] A density functional theory study on mechanism and substituent effects of a base-free and catalyst-free synthesis of functionalized dihydrobenzoxazoles
    Zhang, Huimin
    Bai, Huining
    Guo, Yuen
    Wei, Donghui
    Chen, Hui
    Zhu, Yanyan
    Zhang, Wenjing
    [J]. INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2019, 119 (06)
  • [10] Gold catalyst recycling study in base-free glucose oxidation reaction
    Megias-Sayago, C.
    Bobadilla, L. F.
    Ivanova, S.
    Penkova, A.
    Centeno, M. A.
    Odriozola, J. A.
    [J]. CATALYSIS TODAY, 2018, 301 : 72 - 77