Ag(I) complexes of benzimidazol-2-ylidene ligands: a study of catalytic efficiency towards three-component coupling reactions

被引:10
|
作者
Kilincarslan, Rafet [1 ]
Sadic, Naim [1 ]
Cetinkaya, Bekir [2 ]
机构
[1] Pamukkale Univ, Fac Sci & Letters, Dept Chem, Denizli, Turkey
[2] Ege Univ, Dept Chem, Fac Sci, Izmir, Turkey
关键词
N-heterocyclic carbene; benzimidazol-2-ylidene; coupling reaction; catalyst; N-HETEROCYCLIC-CARBENE; ANTIMICROBIAL ACTIVITY; SILVER COMPLEXES; METAL-COMPLEXES; PALLADIUM(II); PRECURSORS; ALDEHYDE; GOLD(I); IRIDIUM; ALKYNE;
D O I
10.3906/kim-1510-6
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The N-heterocyclic carbene (NHC)-Ag(I) complexes 3a-c were synthesized from benzimidazolium chlorides (2a-c = NHC center dot HCl), incorporating benzyl derivatives and a 2-methoxyethyl group (a: N-3 = 2,4,6-trimethylbenzyl; b: N-3 - 2,3,5,6-tetramethylbenzyl; c: N-3 - pentamethylbenzyl). The compounds were characterized by spectroscopic and elemental analyses. The synthesized NHC-Ag(I) complexes (3a-c) were tested as catalysts for the catalytic three component coupling reaction of aldehyde, alkyne, and amine to propargylamines in various solvents. All complexes were active catalysts for catalytic three-component coupling reactions with good yields under neat and mild conditions (after 4 h, yields of up to 94%).
引用
收藏
页码:681 / 687
页数:7
相关论文
共 50 条
  • [21] Tris(carbene)borate Ligands Featuring Imidazole-2-ylidene, Benzimidazol-2-ylidene, and 1,3,4-Triazol-2-ylidene Donors. Evaluation of Donor Properties in Four-Coordinate {NiNO}10 Complexes
    Munoz, Salvador B., III
    Foster, Wallace K.
    Lin, Hsiu-Jung
    Margarit, Charles G.
    Dickie, Diane A.
    Smith, Jeremy M.
    INORGANIC CHEMISTRY, 2012, 51 (23) : 12660 - 12668
  • [22] Ag(I)/Lewis Acid Cooperatively Promoted Three-Component Coupling for Carbo-Heterofunctionalization of Alkenes
    Tao, Yigao
    Hu, Rong
    Jie, Xiaoming
    Su, Weiping
    ACS CATALYSIS, 2022, 12 (20) : 12670 - 12677
  • [23] Synthesis of palladium complexes derived from imidazolidin-2-ylidene ligands and used for catalytic amination reactions
    Karaca, Emine Ozge
    Gurbuz, Nevin
    Sahin, Onur
    Buyukgungor, Orhan
    Ozdemir, Ismail
    APPLIED ORGANOMETALLIC CHEMISTRY, 2016, 30 (12) : 1050 - 1055
  • [24] Copper(I)-Phosphinite Complexes in Click Cycloadditions: Three-Component Reactions and Preparation of 5-Iodotriazoles
    Perez, Juana M.
    Crosbie, Peter
    Lal, Steven
    Diez-Gonzalez, Silvia
    CHEMCATCHEM, 2016, 8 (13) : 2222 - 2226
  • [25] Direct synthesis of 2-(aminomethyl)indoles through copper(I)-catalyzed domino three-component coupling and cyclization reactions
    Ohno, Hiroaki
    Ohta, Yusuke
    Oishi, Shinya
    Fujii, Nobutaka
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (13) : 2295 - 2298
  • [26] NHC Pd(II) and Ag(I) Complexes: Synthesis, Structure, and Catalytic Activity in Three Types of C-C Coupling Reactions
    Liu, Qing-Xiang
    Hu, Ze-Liang
    Yu, Shao-Cong
    Zhao, Zhi-Xiang
    Wei, Deng-Che
    Li, Hui-Long
    ACS OMEGA, 2018, 3 (04): : 4035 - 4047
  • [27] Copper(I) Complexes with Trispyrazolylmethane Ligands: Synthesis, Characterization, and Catalytic Activity in Cross-Coupling Reactions
    Haldon, Estela
    Alvarez, Eleuterio
    Carmen Nicasio, M.
    Perez, Pedro J.
    INORGANIC CHEMISTRY, 2012, 51 (15) : 8298 - 8306
  • [28] Ag(I)-Catalyzed Three-Component Reaction of 2-Alkynylbenzaldehydes, Amines, and Diazo Compounds
    Xiao, Tiebo
    Peng, Pai
    Xie, Yang
    Wang, Zhao-yang
    Zhou, Lei
    ORGANIC LETTERS, 2015, 17 (17) : 4332 - 4335
  • [29] Preparation and Reactivity Study of Chromium(III), Iron(II), and Cobalt(II) Complexes of 1,3-Bis(imino)benzimidazol-2-ylidene and 1,3-Bis(imino)pyrimidin-2-ylidene
    Al Thagfi, Jameel
    Lavoie, Gino G.
    ORGANOMETALLICS, 2012, 31 (21) : 7351 - 7358
  • [30] Regio- and diastereoselective aldol products through three-component coupling reactions of difluoroboroxy Fischer carbene molybdenum complexes
    Barluenga, J
    Rodríguez, F
    Fañanás, FJ
    Rubio, E
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (20) : 3084 - 3086