Copper(II) Triflate-Catalyzed Three-Component Coupling of Aldehydes, Alkynes and Carbamates

被引:16
作者
Dou, Xiao-Yong [1 ,2 ,3 ]
Qi Shuai [3 ]
He, Liang-Nian [1 ,2 ]
Li, Chao-Jun [3 ]
机构
[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China
[3] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
A(3)-coupling; aldehydes; alkynes; carbamates; copper(II) triflate; HIGHLY ENANTIOSELECTIVE SYNTHESIS; C-H ACTIVATION; TERMINAL ALKYNES; DIRECT-ADDITION; STEREOREGULAR POLY(N-PROPARGYLCARBAMATES); ASYMMETRIC ADDITION; GLYCINE DERIVATIVES; N-PROPARGYLAMIDES; AMINES; IMINES;
D O I
10.1002/adsc.201000379
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A simple and efficient synthesis of propargylcarbamates was developed through a copper(II) triflate-catalyzed coupling of aldehydes, alkynes and carbamates. No co-catalyst or ligand is required.
引用
收藏
页码:2437 / 2440
页数:4
相关论文
共 72 条
  • [1] Preparation of 2,5-disubstituted oxazoles from N-propargylamides
    Arcadi, A
    Cacchi, S
    Cascia, L
    Fabrizi, G
    Marinelli, F
    [J]. ORGANIC LETTERS, 2001, 3 (16) : 2501 - 2504
  • [2] Highly enantioselective access to primary propargylamines: 4-piperidinone as a convenient protecting group
    Aschwanden, Patrick
    Stephenson, Corey R. J.
    Carreira, Erick M.
    [J]. ORGANIC LETTERS, 2006, 8 (11) : 2437 - 2440
  • [3] Click chemistry with O-dimethylpropargylcarbamate for preparation of pH-sensitive functional groups.: A case study
    Bertrand, Philippe
    Gesson, Jean Pierre
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (09) : 3596 - 3599
  • [4] Copper-catalyzed coupling of imines, acid chlorides, and alkynes: A multicomponent route to propargylamides
    Black, DA
    Arndtsen, BA
    [J]. ORGANIC LETTERS, 2004, 6 (07) : 1107 - 1110
  • [5] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity
    Bloch, R
    [J]. CHEMICAL REVIEWS, 1998, 98 (04) : 1407 - 1438
  • [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] Comparative Analysis of Small Molecules and Histone Substrate Analogues as LSD1 Lysine Demethylase Inhibitors
    Culhane, Jeffrey C.
    Wang, Dongqing
    Yen, Paul M.
    Cole, Philip A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) : 3164 - 3176
  • [8] Zn-alkynylide additions to acyl iminiums
    Fischer, C
    Carreira, EM
    [J]. ORGANIC LETTERS, 2004, 6 (09) : 1497 - 1499
  • [9] Synthesis of helical poly(N-propargylamides) carrying azobenzene moieties in side chains.: Reversible arrangement-disarrangement of helical side chain arrays upon photoirradiation keeping helical main chain intact
    Fujii, Torn
    Shiotsuki, Masashi
    Inai, Yoshihito
    Sanda, Fumio
    Masuda, Toshio
    [J]. MACROMOLECULES, 2007, 40 (20) : 7079 - 7088
  • [10] Synthesis and properties of amino acid-based polyacetylenes
    Gao, GZ
    Sanda, F
    Masuda, T
    [J]. MACROMOLECULES, 2003, 36 (11) : 3932 - 3937