Ionic liquid promoted regio- and stereoselective addition of thiols to alkynes and alkenes under organic solvent free condition - A green reaction

被引：0
|
作者：
Ranu, Brindaban C. [1 ]
Chattopadhyay, Kalicharan [1 ]
Ghosh, Sudip [1 ]
Jana, Ranjan [1 ]
机构：
[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, India
来源：
JOURNAL OF THE INDIAN CHEMICAL SOCIETY | 2008年 / 85卷 / 12期
关键词：
Green chemistry; ionic liquid; thiols; alkyne; alkene;
D O I：
暂无
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A simple ionic liquid, 1-methyl-3-pentylimidazolium fluoroborate, [pmIm]BF4, promotes anti-Markovnikov addition of thiols to alkynes providing (Z)- and (E)-vinyl sulfides stereoselectively. The addition of thiols to alkenes in presence of-another ionic liquid, [pmim]Br proceeds through anti-Markovnikov manner, whereas the addition to. vinyl ethers and acetates occurs at more electrophilic C-2 position adjacent to oxygen. The products are obtained in high yields.
引用
收藏
页码：1199 / 1204
页数：6
相关论文
共 50 条
  • [1] Copper Promoted Regio- and Stereoselective Aminochlorination of Alkynes and Alkenes with NFSI
    Wang, Weilin
    Liu, Lingyan
    Chang, Weixing
    Li, Jing
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (34) : 8542 - 8547
  • [2] Base-Promoted Addition of Arylacetonitriles to Terminal Alkynes: Regio- and Stereoselective Access to Disubstituted Acrylonitriles
    Qi, Chaorong
    Peng, Youbin
    Ouyang, Lu
    Ren, Yanwei
    Jiang, Huanfeng
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (08) : 1339 - 1350
  • [3] Regio- and Stereoselective Copper-Catalyzed Addition of Aromatic and Aliphatic Thiols to Terminal and Internal Nonactivated Alkynes
    Trostyanskaya, Inna G.
    Beletskaya, Irina P.
    [J]. SYNLETT, 2012, (04) : 535 - 540
  • [4] Regio- and Stereoselective Synthesis of Dithiocarbonates under Ambient and Solvent-Free Conditions
    Diebler, Johannes
    Spannenberg, Anke
    Werner, Thomas
    [J]. CHEMCATCHEM, 2016, 8 (12) : 2027 - 2030
  • [5] Pronounced chemo-, regio-, and stereoselective [2+2] cycloaddition reaction of allenes toward alkenes and alkynes
    Kimura, M
    Horino, Y
    Wakamiya, Y
    Okajima, T
    Tamaru, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) : 10869 - 10870
  • [6] Ionic liquid-promoted stereoselective synthesis of (Z)-Vinyl bromides by [bmIm]OH under organic solvent-free conditions: A green approach
    Ranu, Brindaban C.
    Banerjee, Subhash
    Gupta, Jhinuk
    [J]. SYNTHETIC COMMUNICATIONS, 2007, 37 (17) : 2869 - 2876
  • [7] Synthesis of 9-arylpolyhydroacridine promoted by ionic liquid under solvent-free condition
    Wei, Jian Hua
    Li, Yi Qun
    Lian, Xi Zhong
    Zhou, Mei Yun
    [J]. CHINESE CHEMICAL LETTERS, 2006, 17 (07) : 874 - 876
  • [8] Synthesis of 9-Arylpolyhydroacridine Promoted by Ionic Liquid Under Solvent-free Condition
    Jian Hua WEI
    [J]. Chinese Chemical Letters, 2006, (07) : 874 - 876
  • [9] NATURAL ORGANIC ACIDS PROMOTED GREEN AND EXPEDITIOUS SYNTHESIS OF COUMARINS UNDER SOLVENT FREE CONDITION
    Rohokale, Sandeep V.
    Kote, Santosh R.
    Thopate, Shankar R.
    [J]. INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 26 (1-2) : 17 - 22
  • [10] Catalysis by an ionic liquid: efficient conjugate addition of thiols to electron deficient alkenes catalyzed by molten tetrabutylammonium bromide under solvent-free conditions
    Ranu, BC
    Dey, SS
    Hajra, A
    [J]. TETRAHEDRON, 2003, 59 (14) : 2417 - 2421
12345