Transition-Metal-Free Addition of Acetylenes to Ketimines: the First Base-Catalyzed Ethynylation of the C=N Bond

被引：30
|
作者：
Bidusenko, Ivan A. [1 ]
Schmidt, Elena Yu [1 ]
Ushakov, Igor A. [1 ]
Trofimov, Boris A. [1 ]
机构：
[1] Russian Acad Sci, Siberian Branch, AE Favorsky Irkutsk Inst Chem, 1 Favorsky Str, Irkutsk 664033, Russia
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 35期
关键词：
Ketimines; Acetylenes; Propargylamines; Superbases; Ethynylation; MULTIFUNCTIONAL DRUGS; COUPLING REACTION; PROPARGYLAMINE; ALKYNE; SINGLE; A(3); NANOPARTICLE; DERIVATIVES; ALZHEIMERS; ALDEHYDES;
D O I：
10.1002/ejoc.201800850
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A one-pot transition metal-free synthesis of propargylamines in good to excellent yield from ketone-derived imines and aryl- and hetarylacetylenes in the presence of KOBut/DMSO superbase system (40 degrees C, 10 min) has been developed. The reaction involves a nucleophilic addition of acetylenic carbanions to the C=N bond, thus for the first time featuring the aza-Favorsky reaction.
引用
收藏
页码：4845 / 4849
页数：5
相关论文
共 50 条
  • [1] Base-Catalyzed Synthesis of Substituted Indazoles under Mild, Transition-Metal-Free Conditions
    Thome, Isabelle
    Besson, Claire
    Kleine, Tillmann
    Bolm, Carsten
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (29) : 7509 - 7513
  • [2] Transition-metal-free and base promoted C-C bond formation via C-N bond cleavage of organoammonium salts
    Zhang, Tao
    Wang, Kunyu
    Ke, Yuting
    Tang, Yuanyuan
    Liu, Long
    Huang, Tianzeng
    Li, Chunya
    Tang, Zhi
    Chen, Tieqiao
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (38) : 8237 - 8240
  • [3] Transition-Metal-Free Activation of Amides by N-C Bond Cleavage
    Li, Guangchen
    Szostak, Michal
    [J]. CHEMICAL RECORD, 2020, 20 (07): : 649 - 659
  • [4] First example of transition-metal-catalyzed addition of aromatic thiols to acetylenes
    [J]. 1600, (114):
  • [5] Transition-metal-free aerobic C-O bond formation via C-N bond cleavage
    Guo, Lirong
    Liu, Fengting
    Wang, Liying
    Yuan, Hairui
    Feng, Lei
    Lu, Haifeng
    Gao, Hongyin
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (09): : 1077 - 1081
  • [6] Transition-Metal-Free Superbase-Catalyzed C-H Vinylation of Aldimines with Acetylenes to 1-Azadienes
    Schmidt, Elena Yu.
    Bidusenko, Ivan A.
    Protsuk, Nadezhda I.
    Demyanov, Yan V.
    Ushakov, Igor A.
    Vashchenko, Alexander V.
    Trofimov, Boris A.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (05): : 3417 - 3425
  • [7] Transition-Metal-Free C-N Bond Activation: Synthesis of α,α-Bis(arylthio) Aldehydes
    Gao, Xu-Hong
    Xu, Wei
    Zhang, Xing-Guo
    Deng, Chen-Liang
    [J]. SYNLETT, 2017, 28 (07) : 841 - 846
  • [8] C–F bond activation under transition-metal-free conditions
    HanJun Ai
    Xingxing Ma
    Qiuling Song
    XiaoFeng Wu
    [J]. Science China(Chemistry), 2021, (10) : 1630 - 1659
  • [9] C–F bond activation under transition-metal-free conditions
    Han-Jun Ai
    Xingxing Ma
    Qiuling Song
    Xiao-Feng Wu
    [J]. Science China Chemistry, 2021, 64 (10) : 1630 - 1659
  • [10] Base-Mediated Transition-Metal-Free Dehydrative C-C and C-N Bond-Forming Reactions from Alcohols
    Porcheddu, Andrea
    Chelucci, Giorgio
    [J]. CHEMICAL RECORD, 2019, 19 (12): : 2398 - 2435
12345