BiCl3-catalyzed propargylic substitution reaction of propargylic alcohols with C-, O-, S- and N-centered nucleophiles

被引：147
作者：
Zhan, Zhuang-ping [1 ]
Yang, Wen-zhen
Yang, Rui-feng
Yu, Jing-liang
Li, Jun-ping
Liu, Hui-juan
机构：
[1] Xiamen Univ, Coll Chem & Chem Engn, Dept Chem, Xiamen 361005, Fujian, Peoples R China
[2] Xiamen Univ, Coll Chem & Chem Engn, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Fujian, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2006年 / 31期
关键词：
D O I：
10.1039/b606470a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A general and efficient BiCl3-catalyzed substitution reaction of propargylic alcohols with carbon and heteroatom-centered nucleophiles such as allyl trimethylsilane, alcohols, aromatic compounds, thiols and amides, leading to the construction of C - C, C - O, C - S and C - N bonds, has been developed.
引用
收藏
页码：3352 / 3354
页数：3
相关论文
共 32 条
  • [1] Synthesis of propargylic ethers via Lewis-acid mediated nucleophilic substitution of propargylic esters
    Bartels, A
    Mahrwald, R
    Quint, S
    [J]. TETRAHEDRON LETTERS, 1999, 40 (33) : 5989 - 5990
  • [2] CAFFYN AJM, 1995, COMPREHENSIVE ORGANO, V12, P685
  • [3] Gold(III)-catalyzed nucleophilic substitution of propargylic alcohols
    Georgy, M
    Boucard, V
    Campagne, JM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (41) : 14180 - 14181
  • [4] Chemistry of propargyldicobalt cations: Recent developments in the Nicholas and related reactions
    Green, JR
    [J]. CURRENT ORGANIC CHEMISTRY, 2001, 5 (07) : 809 - 826
  • [5] Hegedus L., 1984, CATALYST POISONING
  • [6] COPPER(I)-CATALYZED AMINATION OF PROPARGYL ESTERS - SELECTIVE SYNTHESIS OF PROPARGYLAMINES, 1-ALKEN-3-YLAMINES, AND (Z)-ALLYLAMINES
    IMADA, Y
    YUASA, M
    NAKAMURA, I
    MURAHASHI, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) : 2282 - 2284
  • [7] Ruthenium-catalyzed propargylic substitution reaction of propargylic alcohols with thiols: A general synthetic route to propargylic sulfides
    Inada, Y
    Nishibayashi, Y
    Hidai, M
    Uemura, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (51) : 15172 - 15173
  • [8] Rhenium-catalyzed aromatic propargylation
    Kennedy-Smith, JJ
    Young, LA
    Toste, FD
    [J]. ORGANIC LETTERS, 2004, 6 (08) : 1325 - 1327
  • [9] Ruthenium-catalyzed S-propargylation of thiols enables the rapid synthesis of propargylic sulfides
    Kondo, T
    Kanda, Y
    Baba, A
    Fukuda, K
    Nakamura, A
    Wada, K
    Morisaki, Y
    Mitsudo, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) : 12960 - 12961
  • [10] How electrophilic are cobalt carbonyl stabilized propargylium ions?
    Kuhn, O
    Rau, D
    Mayr, H
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (05) : 900 - 907
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