Copper(II) tetrafluoroborate as a novel and highly efficient catalyst for Michael addition of mercaptans to α,β-unsaturated carbonyl compounds

被引:120
|
作者
Garg, SK [1 ]
Kumar, R [1 ]
Chakraborti, AK [1 ]
机构
[1] NIPER, Dept Med Chem, Nagar 160062, Punjab, India
关键词
Michael addition; thiol; alpha; beta-unsaturated carbonyl; copper(II) tetrafluoroborate; catalyst;
D O I
10.1016/j.tetlet.2005.01.051
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper(II) tetrafluoroborate has been found to be a new and highly efficient catalyst for Michael addition of thiols to alpha,beta-unsaturated carbonyl compounds under solvent-free conditions and in H2O at room temperature. The reactions are very fast and are completed in 2 min to 1 h affording high yields. The rate of thiol addition was dependent on the steric hindrance at the beta-carbon of the alpha,beta-unsaturated carbonyl substrate. In the case of chalcones, the reactions are best carried out in MeOH as solvent. (C) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1721 / 1724
页数:4
相关论文
共 50 条
  • [1] A natural phosphate and doped-catalyzed Michael addition of mercaptans to α,β-unsaturated carbonyl compounds
    Abrouki, Y
    Zahouily, M
    Rayadh, A
    Bahlaouan, B
    Sebti, S
    TETRAHEDRON LETTERS, 2002, 43 (49) : 8951 - 8953
  • [2] Copper(II) tetrafluoroborate as a novel and highly efficient catalyst for acetal formation
    Kumar, R
    Chakraborti, AK
    TETRAHEDRON LETTERS, 2005, 46 (48) : 8319 - 8323
  • [3] A facile organocatalyzed Michael addition of pyrazolines to α,β-unsaturated carbonyl compounds
    Xie, Chen
    Lu, Zhijin
    Zhou, Wei
    Han, Jianlin
    Pan, Yi
    TETRAHEDRON LETTERS, 2012, 53 (49) : 6650 - 6653
  • [4] YTTERBIUM TRICYANIDE, A HIGHLY EFFICIENT CATALYST FOR THE ADDITION OF CYANOTRIMETHYLSILANE TO CARBONYL-COMPOUNDS
    MATSUBARA, S
    TAKAI, T
    UTIMOTO, K
    CHEMISTRY LETTERS, 1991, (08) : 1447 - 1450
  • [5] Copper(II) bromide-catalyzed conjugate addition of furans to α,β-unsaturated carbonyl compounds
    Alexander A. Fadeev
    Maxim G. Uchuskin
    Igor V. Trushkov
    Anton S. Makarov
    Chemistry of Heterocyclic Compounds, 2017, 53 : 1286 - 1293
  • [6] Copper(II) bromide-catalyzed conjugate addition of furans to α,β-unsaturated carbonyl compounds
    Fadeev, Alexander A.
    Uchuskin, Maxim G.
    Trushkov, Igor V.
    Makarov, Anton S.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (12) : 1286 - 1293
  • [7] Substitution at the α-carbons of α,β-unsaturated carbonyl compounds:: anti-Michael addition
    Lewandowska, Elzbieta
    TETRAHEDRON, 2007, 63 (10) : 2107 - 2122
  • [8] Michael Addition of Thiols to á, -Unsaturated Carbonyl Compounds Catalyzed by Bifunctional Organocatalysts: Asymmetric Michael Addition and Asymmetric Protonation
    LI BangJing JIANG Lin LIU Min DING LiSheng CHEN YingChun West China School of Pharmacy Sichuan University Chengdu China Chengdu Institute of Biology Chinese Academy of Sciences Chengdu China
    合成化学, 2004, (S1) : 48 - 48
  • [9] A catalytic Michael addition of thiols to α,β-unsaturated carbonyl compounds:: Asymmetric Michael additions and asymmetric protonations
    Emori, E
    Arai, T
    Sasai, H
    Shibasaki, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) : 4043 - 4044
  • [10] Asymmetric Michael addition of arylthiols to α,β-unsaturated carbonyl compounds catalyzed by bifunctional organocatalysts
    Li, BJ
    Jiang, L
    Liu, M
    Chen, YC
    Ding, LS
    Wu, Y
    SYNLETT, 2005, (04) : 603 - 606