Catalytic carbon-sulfur bond formation by amphoteric vanadyl triflate: exploring with thia-Michael addition, thioacetalization, and transthioacetalization reactions

被引：34
作者：
Chen, Chien-Tien [1 ]
Lin, Yow-Dzer [1 ]
Liu, Cheng-Yuan [1 ]
机构：
[1] Natl Taiwan Normal Univ, Dept Chem, Taipei 11650, Taiwan
来源：
TETRAHEDRON | 2009年 / 65卷 / 50期
关键词：
C-S bond formation; Michael addition; Thioacetalization; Vanadyl triflate; ENANTIOSELECTIVE AEROBIC OXIDATION; NUCLEOPHILIC ACYL SUBSTITUTIONS; ASYMMETRIC CONJUGATE ADDITION; HIGHLY EFFICIENT CATALYST; RECYCLABLE CATALYST; CHEMOSELECTIVE THIOACETALIZATION; COPPER(II) TETRAFLUOROBORATE; WATER-TOLERANT; SOFT ACIDS; LEWIS-ACID;
D O I：
10.1016/j.tet.2009.10.012
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of thiols have been examined as protic nucleophiles for Michael-type additions to alpha,beta-unsaturated carbonyls as well as double nucleophilic condensations with aldehydes, ketones, and acetals catalyzed by amphoteric, water-tolerant vanadyl triflate under mild and neutral conditions. The newly developed C-S bond formation protocols were carried out smoothly in good to high yields in a highly chemoselective manner. (C) 2009 Elsevier Ltd. All rights reserved.
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收藏
页码：10470 / 10476
页数：7
相关论文
共 94 条
  • [1] Facile protection of carbonyl compounds as oxathiolanes and transoxathioacetalization of oxyacetals promoted by iron(III) trifluoroacetate or trifluoromethanesulfonate as chemoselective and recyclable catalysts
    Adibi, Hadi
    Jafari, Hadi
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2007, 128 (06) : 679 - 682
  • [2] AKI MMA, 2007, J ORG CHEM, V72, P5411
  • [3] Conjugate addition of indoles and thiols with electron-deficient olefins catalyzed by Bi(OTf)3
    Alam, MM
    Varala, R
    Adapa, SR
    [J]. TETRAHEDRON LETTERS, 2003, 44 (27) : 5115 - 5119
  • [4] Solvent free thioacetalization of carbonyl compounds catalyzed by Cu(OTf)2-SiO2
    Anand, RV
    Saravanan, P
    Singh, VK
    [J]. SYNLETT, 1999, (04) : 415 - 416
  • [5] Antitumor activity of KF22678, a novel thioester derivative of leinamycin
    Ashizawa, T
    Kawashima, K
    Kanda, Y
    Gomi, K
    Okabe, M
    Ueda, K
    Tamaoki, T
    [J]. ANTI-CANCER DRUGS, 1999, 10 (09) : 829 - 836
  • [6] Iron(III) fluoride: A highly efficient and versatile catalyst for the protection of carbonyl compounds under solvent-free conditions
    Bandgar, BP
    Kamble, VT
    Kulkarni, A
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 2005, 58 (08) : 607 - 610
  • [7] Sequential one-pot InBr3-catalyzed 1,4-then 1,2-nucleophilic addition to enones
    Bandini, M
    Cozzi, PG
    Giacomini, M
    Melchiorre, P
    Selva, S
    Umani-Ronchi, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (11) : 3700 - 3704
  • [8] Copper(II) tetrafluoroborate as an extremely efficient catalyst for 1,3-dithiolane/dithiane formation from carbonyl compounds under solvent-free conditions at room temperature
    Besra, RC
    Rudrawar, S
    Chakraborti, AK
    [J]. TETRAHEDRON LETTERS, 2005, 46 (37) : 6213 - 6217
  • [9] Breit B, 1998, ANGEW CHEM INT EDIT, V37, P453, DOI 10.1002/(SICI)1521-3773(19980302)37:4<453::AID-ANIE453>3.0.CO
  • [10] 2-M
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