Copper catalysed cross-dehydrogenative coupling (CDC) reaction of 4-thiazolidinone with terminal alkyne

被引:10
|
作者
Shaikh, Mohammedumar M. [1 ]
Patel, Anuj P. [1 ]
Chikhalia, Kishor H. [2 ]
机构
[1] Gujarat Univ, Sch Sci, Dept Chem, Ahmadabad 380009, Gujarat, India
[2] Veer Narmad South Gujarat Univ, Dept Chem, Surat 395007, Gujarat, India
关键词
Cross dehydrogenative coupling (CDC); sp(3)(C)-sp(C) bond; 4-Thiazolidinone; DFT study; C-C BOND; EFFICIENT ALKYNYLATION; PUMMERER REACTION; FUNCTIONALIZATION; STRATEGY; MECHANISM; TOSYLHYDRAZONES; ABSTRACTION; ALKYLZINC; AMINATION;
D O I
10.1016/j.tet.2018.10.068
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cross dehydrogenative coupling (CDC) strategy has been employed for C-alkynylation of 4-thiazolidinone with terminal alkyne under copper catalysis. Present reaction involves coupling of C(sp(3)) adjacent to sulfur of 4-thiazolidinone with C(sp) of terminal alkyne under CDC strategy is unprecedented to the best of our knowledge. Significant functional group tolerance, considerable yield and DFT study for mechanism make this synthetic task more interesting and compatible. (C) 2018 Elsevier Ltd. All rights reserved.
引用
下载
收藏
页码:475 / 485
页数:11
相关论文
共 50 条
  • [11] Copper-Mediated Cross-Dehydrogenative Coupling Reaction of Pyrrole and Indole Derivatives with Thiols
    Ma, Wenbo
    Xu, Yue
    Gu, Qilin
    Zheng, Tao
    Gu, Linghui
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (08)
  • [12] Copper-based MetalOrganic Frameworks as Heterogeneous Catalysts for Cross-Dehydrogenative Coupling Reaction
    Karthik, Veerappan
    Rokhum, Samuel Lalthazuala
    Dhakshinamoorthy, Amarajothi
    CHEMISTRYSELECT, 2023, 8 (37):
  • [13] Copper-Catalyzed Cross-Dehydrogenative Coupling (CDC) of Alkynes and Benzylic C-H Bonds
    Correia, Camille A.
    Li, Chao-Jun
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (09) : 1446 - 1450
  • [14] Unique regioselectivity of the Pd-catalysed cross-dehydrogenative coupling reaction of simple polyaromatic hydrocarbons with polyfluoroarenes
    Sato, Ryota
    Lida, Tomoki
    Kanbara, Takaki
    Kuwabara, Junpei
    CHEMICAL COMMUNICATIONS, 2022, 58 (82) : 11511 - 11514
  • [15] Electrochemically induced cross-dehydrogenative coupling (CDC) reaction. An efficient electrochemical method for the synthesis of dicoumarols
    Dadpou, Bita
    Nematollahi, Davood
    RSC ADVANCES, 2014, 4 (92) : 50365 - 50368
  • [16] An efficient alkynylation of 4-thiazolidinone with terminal alkyne under C-H functionalisation
    Shaikh, Mohammed Umar M.
    Mudaliar, Sulochana S.
    Chikhalia, Kishor H.
    RSC ADVANCES, 2016, 6 (56): : 50780 - 50785
  • [17] Bu4NI-Catalyzed C-O Bond Formation by Using a Cross-Dehydrogenative Coupling (CDC) Reaction
    Chen, Long
    Shi, Erbo
    Liu, Zhaojun
    Chen, Shulin
    Wei, Wei
    Li, Hong
    Xu, Kai
    Wan, Xiaobing
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (15) : 4085 - 4089
  • [18] Copper(i)-catalysed intramolecular hydroarylation-redox cross-dehydrogenative coupling of N-propargylanilines with phosphites
    Li, Guangzhe
    Yu, Guo
    Wang, Chengdong
    Morita, Taiki
    Zhang, Xuhai
    Nakamura, Hiroyuki
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 20 (01) : 113 - 116
  • [19] Copper-catalyzed oxidative cross-dehydrogenative coupling of 2H-chromenes and terminal alkynes
    Yang, Fei
    Li, Yangshan
    Floreancig, Paul E.
    Li, Xiaoyan
    Liu, Lei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (28) : 5144 - 5149
  • [20] Cross-dehydrogenative coupling reaction using copper oxide impregnated on magnetite in deep eutectic solvents
    Marset, Xavier
    Perez, Juana M.
    Ramon, Diego J.
    GREEN CHEMISTRY, 2016, 18 (03) : 826 - 833