Transition-Metal Catalyzed Coupling Reactions of gem-Dibromovinyl Derivatives

被引:2
|
作者
Liang Luqi [1 ,2 ]
Zhang Lizhi [2 ]
Peng Yongli [1 ]
Liu Hui [1 ,2 ]
机构
[1] Wuhan Inst Technol, Sch Mat Sci & Engn, Wuhan 430205, Peoples R China
[2] Shandong Univ Technol, Sch Chem Engn, Zibo 255049, Shandong, Peoples R China
基金
中国国家自然科学基金;
关键词
gem-dibromovinyl derivative; alkynyl intermediate; transition metal catalysis; coupling reaction; DIBROMOALKENES; ALKYNES; ALKYNYLATION; ACCESS;
D O I
10.6023/cjoc202110026
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
gem-Dibromovinyl derivatives are valuable synthetic tools in organic chemistry, which have been widely applied in the construction of founctionalized molecules. In the past few years, metal-catalyzed (such as Pd, Cu, Ag, Au and Ni) transformations with gem-dibromovinyl derivatives have been developed and become a powerful tool for the synthesis of alkynes, chromenes, indoles, benzindole, benzothiophene and other benzo-fused heterocycles with important physiological activity. The progresses in transition-metal-catalyzed transformations of gem-dibromoviny derivatives since 2013 are summarized.
引用
收藏
页码:1033 / 1060
页数:28
相关论文
共 33 条
  • [1] Direct Alkynylation of 3H-Imidazo[4,5-b]pyridines Using gem-Dibromoalkenes as Alkynes Source
    Aziz, Jessy
    Baladi, Tom
    Piguel, Sandrine
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (10): : 4122 - 4133
  • [2] Copper/Palladium-Catalyzed Cyclization/Cross-Coupling Cascade Reaction of 2-gem-Dibromovinyl Aryl Selenides: Synthesis of 2-Substituted Benzo[b]selenophenes
    Bilheri, Filipe N.
    Pistoia, Renan P.
    Back, Davi F.
    Zeni, Gilson
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (23) : 4208 - 4216
  • [3] Synthesis and Metal-Catalyzed Reactions of gem-Dihalovinyl Systems
    Chelucci, Giorgio
    [J]. CHEMICAL REVIEWS, 2012, 112 (03) : 1344 - 1462
  • [4] COREY EJ, 1972, TETRAHEDRON LETT, P3769
  • [5] Pd-catalyzed tandem C-N/C-C coupling of gem-dihalovinyl systems: A modular synthesis of 2-substituted indoles
    Fang, YQ
    Lautens, M
    [J]. ORGANIC LETTERS, 2005, 7 (16) : 3549 - 3552
  • [6] Counter Ion Effect in Au/Ag-Catalyzed Chemoselective 6-endo-dig N- and O-Cyclizations of Enyne-Urea System: Diversity-Oriented Synthesis of Annulated Indoles
    Gupta, Sahaj
    Koley, Dipankar
    Ravikumar, Krishnan
    Kundu, Bijoy
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (17): : 8624 - 8633
  • [7] Synthesis of diynes from 1-(2,2-dibromovinyl)-2-(phenylethynyl)benzene and imidazole/benzimidazole via a CuI/Pd(OAc)2 catalysed cascade reaction
    He Hua-Feng
    Ye Yang
    Jiang Yongwen
    Bao Weiliang
    [J]. JOURNAL OF CHEMICAL RESEARCH, 2014, (07) : 399 - 403
  • [8] Synthesis of 6H-isoindolo[2,1-a]indol-6-ones through a sequential copper-catalyzed C-N coupling and palladium-catalyzed C-H activation reaction
    He, Hua-Feng
    Dong, Sheng
    Chen, Yi
    Yang, Yang
    Le, Yueqin
    Bao, Weiliang
    [J]. TETRAHEDRON, 2012, 68 (14) : 3112 - 3116
  • [9] Domino C-H functionalization reactions of gem-dibromoolefins: synthesis of N-fused benzo[c]carbazoles
    Huang, Richard Y.
    Franke, Patrick T.
    Nicolaus, Norman
    Lautens, Mark
    [J]. TETRAHEDRON, 2013, 69 (22) : 4395 - 4402
  • [10] Copper-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylates with 1,1-Dibromo-1-alkenes
    Huang, Zheng
    Shang, Rui
    Zhang, Zi-Rong
    Tan, Xiao-Dan
    Xiao, Xiao
    Fu, Yao
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (09): : 4551 - 4557