Indium-mediated Barbier-type allylation reaction in PEG400 and PEG400/H2O

被引：5
作者：
Du, Zhengyin [1 ]
Wang, Fen
Zhou, Wanwei
Wang, Jin-Xian
机构：
[1] NW Normal Univ, Key Lab Ecoenvironm Related Polymer Mat, Minist Educ, Key Lab Polymer Mat Gansu Prov, Lanzhou 730070, Peoples R China
来源：
JOURNAL OF CHEMICAL RESEARCH | 2010年 / 08期
关键词：
indium; allylation; homoallyl alcohols; PEG400; aqueous reaction; green synthesis; AQUEOUS-MEDIA; CARBONYL-COMPOUNDS; ORGANOMETALLIC REACTIONS; ORGANIC-SYNTHESIS; ALDEHYDES; IMINES; SYSTEM; WATER;
D O I：
10.3184/030823410X12813608471242
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A green method for the allylation of aldehydes with allyl bromide mediated by indium in polyethylene glycol 400 (PEG400) and PEG400/H2O is described. Aldehydes with different substituents afforded the corresponding homoallylic alcohols in good to excellent yields. Comparative studies show that water promoted this reaction in PEG 400.
引用
收藏
页码：475 / 477
页数：3
相关论文
共 22 条
  • [1] Anastas P. T., 1988, GREEN CHEM FRONTIERS
  • [2] Indium-catalyzed allylation of carbonyl compounds with the Mn/TMSCl system
    Augé, J
    Lubin-Germain, N
    Thiaw-Woaye, A
    [J]. TETRAHEDRON LETTERS, 1999, 40 (52) : 9245 - 9247
  • [3] Indium-catalyzed Barbier allylation reaction
    Augé, J
    Lubin-Germain, N
    Marque, S
    Seghrouchni, L
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 679 (01) : 79 - 83
  • [4] Potassium allyl- and crotyltrifluoroborates: Stable and efficient agents for allylation and crotylation
    Batey, RA
    Thadani, AN
    Smil, DV
    [J]. TETRAHEDRON LETTERS, 1999, 40 (23) : 4289 - 4292
  • [5] Iron-mediated allylation of aryl aldehydes in aqueous media
    Chan, TC
    Lau, CP
    Chan, TH
    [J]. TETRAHEDRON LETTERS, 2004, 45 (21) : 4189 - 4191
  • [6] Indium-mediated organometallic reactions in aqueous media: The nature of the allylindium intermediate
    Chan, TH
    Yang, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) : 3228 - 3229
  • [7] Polyethylene glycol and solutions of polyethylene glycol as green reaction media
    Chen, J
    Spear, SK
    Huddleston, JG
    Rogers, RD
    [J]. GREEN CHEMISTRY, 2005, 7 (02) : 64 - 82
  • [8] Catalytic, Nucleophilic Allylation of Aldehydes with Allyl Acetate
    Denmark, Scott E.
    Nguyen, Son T.
    [J]. ORGANIC LETTERS, 2009, 11 (03) : 781 - 784
  • [9] Du ZY, 2010, PROG CHEM, V22, P71
  • [10] Asymmetric indium-mediated Barbier-type allylation reactions with ketones to form homoallylic alcohol products
    Haddad, Terra D.
    Hirayama, Lacie C.
    Taynton, Philip
    Singaram, Bakthan
    [J]. TETRAHEDRON LETTERS, 2008, 49 (03) : 508 - 511
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