Iodine-mediated regio- and stereoselective iodothiocyanation of alkynes in aqueous ethanol

被引:19
|
作者
Zeng, Xianghua [1 ]
Chen, Lu [2 ]
机构
[1] Jiaxing Univ, Coll Biol Chem Sci & Engn, 118 Jiahang Rd, Jiaxing 314001, Peoples R China
[2] Wuyi Univ, Sch Chem & Environm Engn, Jiangmen 529090, Guangdong, Peoples R China
关键词
REGIOSELECTIVE THIOCYANATION; DIRECT ARYLATION; BOND FORMATION; PALLADIUM; ALKENES; ACCESS; HETEROCYCLES; FACILE; THIOCYANOOXYGENATION; HETEROAROMATICS;
D O I
10.1039/c8ob02216j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Iodothiocyanation of alkynes with ammonium thiocyanate (NH4SCN) and molecular iodine (I-2) has been demonstrated in aqueous ethanol, which enables efficient synthesis of a series of functional -iodo vinylthiocyanates in good to excellent yields under mild reaction conditions without the need for any protection.
引用
收藏
页码:7557 / 7560
页数:4
相关论文
共 50 条
  • [21] Regio- and stereoselective enyne cross metathesis of silylated internal alkynes
    1600, American Chemical Society, Columbus, United States (126):
  • [22] Highly Regio- and Stereoselective Intermolecular Seleno- and Thioamination of Alkynes
    Zheng, Guangfan
    Zhao, Jinbo
    Li, Zhanyu
    Zhang, Qiao
    Sun, Jiaqiong
    Sun, Haizhu
    Zhang, Qian
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (10) : 3513 - 3518
  • [23] Regio- and stereoselective oxidative conversion of alkynes to sulfenylated α,β-unsaturated carbonyls
    Tang, Meizhong
    Wang, Ye-Xin
    Huang, Shenlin
    Xie, Lan-Gui
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (10) : 2416 - 2421
  • [24] Regio- and stereoselective decarbonylative carbostannylation of alkynes catalyzed by Pd/C
    Nakao, Y
    Satoh, J
    Shirakawa, E
    Hiyama, T
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (14) : 2271 - 2274
  • [25] Pt-catalyzed regio- and stereoselective pyridylthiolation of terminal alkynes
    Hirai, T
    Kuniyasu, H
    Kambe, N
    TETRAHEDRON LETTERS, 2005, 46 (01) : 117 - 119
  • [26] Cesium Hydroxide-mediated Regio- and Stereoselective Hydroamidation of Internal Aryl Alkynes with Primary Amides
    Yamamoto, Chiaki
    Hirano, Koji
    Miura, Masahiro
    CHEMISTRY LETTERS, 2017, 46 (07) : 1048 - 1050
  • [27] Organoboron-Mediated Regio- and Stereoselective Glycosylation
    Takahashi, Daisuke
    TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY, 2015, 27 (154) : 61 - 62
  • [28] Iron(III) Chloride-Mediated Regio- and Stereoselective Chlorosulfonylation of Alkynes and Alkenes with Sodium Sulfinates
    Zeng, Kui
    Chen, Lang
    Chen, Yi
    Liu, Yongping
    Zhou, Yongbo
    Au, Chak-Tong
    Yin, Shuang-Feng
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (05) : 841 - 847
  • [29] Copper Nitrate Mediated Regio- and Stereoselective Difunctionalization of Alkynes: A Direct Approach to α-Chloro-β-nitroolefins
    Gao, Mingchun
    Xu, Bin
    ORGANIC LETTERS, 2016, 18 (18) : 4746 - 4749
  • [30] Regio- and stereoselective iodoarylation of arylacetylenes using molecular iodine promoted by hypervalent iodine
    Rahman, Md. Ataur
    Kitamura, Tsugio
    TETRAHEDRON LETTERS, 2009, 50 (33) : 4759 - 4761