Palladium N-heterocyclic carbene catalyzed regioselective C-H halogenation of 1-aryl-3-methyl-1H-pyrazol-5(4H)-ones using N-halosuccinimides (NXS)

被引:26
|
作者
Purohit, Vishal B. [1 ]
Karad, Sharad C. [1 ]
Patel, Kirit H. [1 ]
Raval, Dipak K. [1 ]
机构
[1] Sardar Patel Univ, Dept Chem, Vallabh Vidyanagar 388120, Gujarat, India
关键词
SELECTIVE ORTHO-BROMINATION; CROSS-COUPLING REACTIONS; ONE-POT SYNTHESIS; DERIVATIVES BEARING; BOND FORMATION; IONIC LIQUIDS; COMPLEXES; SCAFFOLD; SP(2); EFFICIENT;
D O I
10.1039/c5cy00137d
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A novel palladium N-heterocyclic carbene [Pd(NHC)Cl-2] complex of vitamin B-1 was synthesized and characterized by H-1 NMR, EDX, FT-IR and UV-visible spectroscopy. The complex was used as a catalyst for regioselective ortho-C-H chlorination/bromination of 1-aryl-3-methyl-1H-pyrazol-5(4H)-ones via C-H bond activation utilizing Ag2O as the effective terminal additive. The catalyst was easy to prepare, efficient and found to be highly regioselective, affording the target products in moderate to excellent yields.
引用
收藏
页码:3113 / 3118
页数:6
相关论文
共 50 条
  • [1] Palladium N-heterocyclic carbene catalyzed regioselective thiolation of 1-aryl-3-methyl-1H-pyrazol-5(4H)-ones using aryl thiols
    Purohit, Vishal B.
    Karad, Sharad C.
    Patel, Kirit H.
    Raval, Dipak K.
    TETRAHEDRON, 2016, 72 (08) : 1114 - 1119
  • [2] Palladium N-heterocyclic carbene catalyzed expected and unexpected C-C and C-N functionalization reactions of 1-aryl-3-methyl-1H-pyrazol-5(4H)-ones
    Purohit, Vishal B.
    Karad, Sharad C.
    Patel, Kirit H.
    Raval, Dipak K.
    RSC ADVANCES, 2016, 6 (112): : 111139 - 111143
  • [3] Cu-Catalyzed Aryl C-H Halogenation Using N-Halosuccinimides via Assistance of Benzoic Acid
    Du Zhijun
    Gao Lianxun
    Lin Yingjie
    CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2015, 31 (02) : 167 - 170
  • [4] Cu-catalyzed aryl C-H halogenation using N-halosuccinimides via assistance of benzoic acid
    Zhijun Du
    Lianxun Gao
    Yingjie Lin
    Chemical Research in Chinese Universities, 2015, 31 : 167 - 170
  • [5] Rh(III)-Catalyzed Intermolecular C-H Amination of 1-Aryl-1H-pyrazol-5(4H)-ones with Alkylamines
    Wu, Kui
    Fan, Zhoulong
    Xue, Yu
    Yao, Qizheng
    Zhang, Ao
    ORGANIC LETTERS, 2014, 16 (01) : 42 - 45
  • [6] Advance of N-Halosuccinimides in Transition-Metal-Catalyzed Halogenation of Aromatic C-H Bonds
    Luo, Junfei
    Xu, Xing
    Zhao, Yanchao
    Liang, Hongze
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (11) : 2873 - 2882
  • [7] N-heterocyclic carbene intermediates in Rh catalyzed C-H functionalization.
    Wiedemann, SH
    Bergman, RG
    Ellman, JA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U817 - U817
  • [8] Palladium(ii)/N-heterocyclic carbene (NHC) catalyzed direct C-H arylation of heteroarenes with different aryl bromides and chlorides
    Bensalah, Donia
    Mansour, Lamjed
    Sauthier, Mathieu
    Gurbuz, Nevin
    Ozdemir, Ismail
    Koko, Waleed S.
    Gatri, Rafik
    Hamdi, Naceur
    NEW JOURNAL OF CHEMISTRY, 2023, 47 (44) : 20435 - 20455
  • [9] Palladium(II)/N-Heterocyclic Carbene-Catalyzed Direct C-H Acylation of Heteroarenes with N-Acylsaccharins
    Karthik, Shanmugam
    Gandhi, Thirumanavelan
    ORGANIC LETTERS, 2017, 19 (19) : 5486 - 5489
  • [10] Carboxylation of N-H/C-H Bonds Using N-Heterocyclic Carbene Copper(I) Complexes
    Boogaerts, Ine I. F.
    Fortman, George C.
    Furst, Marc R. L.
    Cazin, Catherine S. J.
    Nolan, Steven P.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (46) : 8674 - 8677