A convenient procedure for bismuth-mediated Barbier-type allylation of aldehydes in water containing fluoride ions

被引:38
作者
Smith, K
Lock, S
El-Hiti, GA
Wada, M
Miyoshi, N
机构
[1] Univ Coll Swansea, Ctr Clean Chem, Dept Chem, Swansea SA2 8PP, W Glam, Wales
[2] Univ Tokushima, Fac Integrated Arts & Sci, Dept Chem, Tokushima 770, Japan
[3] Tanta Univ, Fac Sci, Dept Chem, Tanta 31527, Egypt
关键词
D O I
10.1039/b400179f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new and convenient procedure for synthesis of homoallylic alcohols in generally good to excellent yields has been developed. The bismuth-mediated Barbier-type allylation of aldehydes ( aromatic, aliphatic, alicyclic and heterocyclic) with allyl bromide has been carried out smoothly in water in the presence of fluoride ions.
引用
收藏
页码:935 / 938
页数:4
相关论文
共 48 条
  • [31] Development of a system for clean and regioselective mononitration of aromatic compounds involving a microporous solid, dinitrogen tetroxide and air
    Smith, K
    Almeer, S
    Black, SJ
    Peters, C
    [J]. JOURNAL OF MATERIALS CHEMISTRY, 2002, 12 (11) : 3285 - 3289
  • [32] A novel method for the nitration of simple aromatic compounds
    Smith, K
    Musson, A
    DeBoos, GA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) : 8448 - 8454
  • [33] A novel method for the nitration of deactivated aromatic compounds
    Smith, K
    Gibbins, T
    Millar, RW
    Claridge, RP
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (16): : 2753 - 2758
  • [34] Lithiation and side-chain substitution of 3-alkyl-1H-quinoxalin-2-ones
    Smith, K
    El-Hiti, GA
    Mahgoub, SA
    [J]. SYNTHESIS-STUTTGART, 2003, (15): : 2345 - 2348
  • [35] Lithiation of 3-(acylamino)-2-unsubstituted-, 3-(acylamino)-2-ethyl-, and 3-(acylamino)-2-propyl-4(3H)-quinazolinones: Convenient syntheses of more complex quinazolinones
    Smith, K
    ElHiti, GA
    AbdelMegeed, MF
    Abdo, MA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) : 647 - 655
  • [36] REGIOSPECIFIC ELECTROPHILIC SUBSTITUTION OF AMINOQUINAZOLINONES - DIRECTED LITHIATION OF 3-(PIVALOYLAMINO)-2-METHYLQUINAZOLIN-4(3H)-ONES AND 3-(ACETYLAMINO)-2-METHYLQUINAZOLIN-4(3H)-ONES
    SMITH, K
    ELHITI, GA
    ABDO, MA
    ABDELMEGEED, MF
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (08): : 1029 - 1033
  • [37] Selective mono-chlorination of aromatic compounds under mild conditions by tert-butyl hypochlorite in the presence of zeolites
    Smith, K
    Butters, M
    Paget, WE
    Goubet, D
    Fromentin, E
    Nay, B
    [J]. GREEN CHEMISTRY, 1999, 1 (02) : 83 - 90
  • [38] Synthesis of aromatic ketones by acylation of aryl ethers with carboxylic anhydrides in the presence of zeolite H-β (H-BEA) in the absence of solvent
    Smith, K
    Zhenhua, Z
    Hodgson, PKG
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1998, 134 (1-3) : 121 - 128
  • [39] Selective para-bromination of phenyl acetate -: under the control of zeolites, bases, acetic anhydride or metal acetates in the liquid phase
    Smith, K
    He, P
    Taylor, A
    [J]. GREEN CHEMISTRY, 1999, 1 (01) : 35 - 38
  • [40] Carbonylation of various organolithium reagents.: A novel approach to heterocycles via intramolecular trapping of aromatic acyllithiums
    Smith, K
    El-Hiti, GA
    Pritchard, GJ
    Hamilton, A
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (16): : 2299 - 2303