Efficient synthesis of propargylamines from terminal alkynes, dichloromethane and tertiary amines over silver catalysts

被引:44
作者
Chen, Xiuling [1 ]
Chen, Tieqiao [1 ]
Zhou, Yongbo [1 ]
Au, Chak-Tong [1 ,2 ]
Han, Li-Biao [1 ]
Yin, Shuang-Feng [1 ]
机构
[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Hunan, Peoples R China
[2] Hong Kong Baptist Univ, Dept Chem, Kowloon Tong, Hong Kong, Peoples R China
关键词
3-COMPONENT COUPLING REACTION; H BONDS ADJACENT; C-H; DIRECT-ADDITION; ENANTIOSELECTIVE SYNTHESIS; MILD CONDITIONS; COPPER; ALDEHYDE; ACTIVATION; ALLENES;
D O I
10.1039/c3ob41878b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple, efficient and highly functional group compatible method for the synthesis of propargylamines from terminal alkynes, dichloromethane and tertiary amines using silver catalysts has been developed.
引用
收藏
页码:247 / 250
页数:4
相关论文
共 51 条
  • [1] Mechanistic Insights into the One-Pot Synthesis of Propargylamines from Terminal Alkynes and Amines in Chlorinated Solvents Catalyzed by Gold Compounds and Nanoparticles
    Aguilar, David
    Contel, Maria
    Urriolabeitia, Esteban P.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (30) : 9287 - 9296
  • [2] THE QUARTERNIZATION OF TERTIARY-AMINES WITH DIHALOMETHANE
    ALMARZOQI, B
    GEORGE, AV
    ISAACS, NS
    [J]. TETRAHEDRON, 1986, 42 (02) : 601 - 607
  • [3] Efficient ruthenium and copper cocatalzyed five-component coupling to form dipropargyl amines under mild conditions in water
    Bonfield, E. Ryan
    Li, Chao-Jun
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (03) : 435 - 437
  • [4] BRYSON TA, 1980, J ORG CHEM, V45, P524, DOI 10.1021/jo01291a032
  • [5] Iron(III)-Catalyzed and Air-Mediated Tandem Reaction of Aldehydes, Alkynes and Amines: An Efficient Approach to Substituted Quinolines
    Cao, Ke
    Zhang, Fu-Min
    Tu, Yong-Qiang
    Zhuo, Xiao-Tao
    Fan, Chun-An
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (26) : 6332 - 6334
  • [6] Iron-catalyzed three-component coupling of aldehyde, alkyne, and amine under neat conditions in air
    Chen, Wen-Wen
    Nguyen, Rene V.
    Li, Chao-Jun
    [J]. TETRAHEDRON LETTERS, 2009, 50 (24) : 2895 - 2898
  • [7] REACTIONS OF SILYL ENOL ETHERS AND LACTONE ENOLATES WITH DIMETHYL(METHYLENE)AMMONIUM IODIDE - BIS-ALPHA-METHYLENATION OF PRE-VERNOLEPIN AND PRE-VERNOMENIN
    DANISHEFSKY, S
    KITAHARA, T
    MCKEE, R
    SCHUDA, PF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (21) : 6715 - 6717
  • [8] Efficient three-component coupling catalysed by mesoporous copper-aluminum based nanocomposites
    Dulle, Jana
    Thirunavukkarasu, K.
    Mittelmeijer-Hazeleger, Marjo C.
    Andreeva, Daria V.
    Shiju, N. Raveendran
    Rothenberg, Gadi
    [J]. GREEN CHEMISTRY, 2013, 15 (05) : 1238 - 1243
  • [9] Direct addition of TMS-acetylene to aldimines catalyzed by a simple, commercially available Ir(I) complex
    Fischer, C
    Carreira, EM
    [J]. ORGANIC LETTERS, 2001, 3 (26) : 4319 - 4321
  • [10] Kinetic evidence for a novel, Grob-like substitution fragmentation mechanism for the reaction of nucleophiles with trialkylammoniomethyl halides
    Fletcher, MO
    Zhang, L
    Vu, QY
    Dolbier, WR
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (06): : 1187 - 1192