NaOH-promoted reaction of 1,1-dihaloalkenes and 1H-azoles: synthesis of dihetaryl substituted alkenes

被引:6
|
作者
Zhang, Chen [1 ]
Shi, Yu-Long [1 ]
Zhang, Li-Yu [1 ]
Yuan, Dong-Peng [2 ]
Ban, Meng-Tao [1 ]
Zheng, Jia-Yao [1 ]
Liu, Deng-Hui [1 ]
Guo, Shun-Na [1 ]
Cui, Dong-Mei [2 ]
机构
[1] Zhejiang Univ, Coll Pharmaceut Sci, Hangzhou 310058, Zhejiang, Peoples R China
[2] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Zhejiang, Peoples R China
关键词
CROSS-COUPLING REACTIONS; RUTHENIUM-CATALYZED SYNTHESIS; ULLMANN-TYPE REACTION; VINYL BROMIDES; 1,1-DIBROMO-1-ALKENES; IMIDAZOLES; PHENOLS; LIGANDS; HALIDES; NUCLEOPHILES;
D O I
10.1039/c8nj02756k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient NaOH-promoted synthesis of dihetaryl substituted alkenes from 1,1-dihaloalkenes and 1H-azoles under mild conditions has been developed. The reaction occurred in moderate to good yields and tolerated aliphatic, heterocyclic, and aryl substituted 1,1-dihaloalkenes containing functionalities such as nitriles, ethers, and halogens. Imidazoles and triazoles also afforded the desired products.
引用
收藏
页码:17732 / 17739
页数:8
相关论文
共 50 条
  • [1] Reaction of 1H-azoles with 2-hydroxybenzyl alcohols
    Sidorina N.E.
    Osyanin V.A.
    [J]. Chemistry of Heterocyclic Compounds, 2007, 43 (8) : 1065 - 1071
  • [2] 1H-Azoles in the reaction with 2-hydroxybenzyl alcohols
    Sidorina, N. E.
    Osyanin, V. A.
    [J]. KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2007, (08): : 1256 - 1263
  • [3] Theoretical study on the lithium-halogen exchange reaction of 1,1-dihaloalkenes with methyllithium and the nucleophilic substitution reaction of the resulting α-halo alkenyllithiums
    Ando, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05): : 1837 - 1850
  • [4] Synthesis of 1-(pyrrolidin-2-ylmethyl)-1H-azoles and their piperidine-derived homologues
    Zhersh, Sergey
    Karpenko, Oleksandr V.
    Ripenko, Vasyl
    Tolmachev, Andrey A.
    Grygorenko, Oleksandr O.
    [J]. CENTRAL EUROPEAN JOURNAL OF CHEMISTRY, 2014, 12 (01): : 67 - 73
  • [5] Suzuki arylation of 1,1-dibromo-1-alkenes: Synthesis of tetra-substituted alkenes
    Bauer, A
    Miller, MW
    Vice, SF
    McCombie, SW
    [J]. SYNLETT, 2001, (02) : 254 - 256
  • [6] A NEW SYNTHESIS OF 1,1-BIS(TRIFLUOROMETHYL)-SUBSTITUTED ALKENES
    HANACK, M
    KORHUMMEL, C
    [J]. SYNTHESIS-STUTTGART, 1987, (10): : 944 - 947
  • [7] REACTION OF ALKYLIDENETRIPHENYLPHOSPHORANES WITH CHLORODIFLUOROMETHANE - SYNTHESIS OF 1,1-DIFLUORO-1-ALKENES
    WHEATON, GA
    BURTON, DJ
    [J]. TETRAHEDRON LETTERS, 1976, (12) : 895 - 898
  • [8] Synthesis and fungicidal activities of 1-[(2,2-diaryl-1,3-dioxolan-4-yl)methyl]-1H-azoles
    Talismanov, V. S.
    Popkov, S. V.
    [J]. RUSSIAN CHEMICAL BULLETIN, 2007, 56 (05) : 975 - 979
  • [9] Synthesis and fungicidal activities of 1-[(2,2-diaryl-1,3-dioxolan-4-yl)methyl]-1H-azoles
    V. S. Talismanov
    S. V. Popkov
    [J]. Russian Chemical Bulletin, 2007, 56 : 975 - 979
  • [10] Synthesis of 1,1-Diboryl Alkenes Using the Boryl-Heck Reaction
    Idowu, Olamide O.
    Hayes, Jacob C.
    Reid, William B.
    Watson, Donald A.
    [J]. ORGANIC LETTERS, 2021, 23 (12) : 4838 - 4842