Article

CuO Nanoparticles Catalyzed C-N, C-O, and C-S Cross-Coupling Reactions: Scope and Mechanism

Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India.
The Journal of Organic Chemistry (Impact Factor: 4.64). 02/2009; 74(5):1971-6. DOI: 10.1021/jo8024253
Source: PubMed

ABSTRACT CuO nanoparticles have been studied for C-N, C-O, and C-S bond formations via cross-coupling reactions of nitrogen, oxygen, and sulfur nucleophiles with aryl halides. Amides, amines, imidazoles, phenols, alcohols and thiols undergo reactions with aryl iodides in the presence of a base such as KOH, Cs(2)CO(3), and K(2)CO(3) at moderate temperature. The procedure is simple, general, ligand-free, and efficient to afford the cross-coupled products in high yield.

3 Followers
 · 
501 Views
  • [Show abstract] [Hide abstract]
    ABSTRACT: An efficient nanocrystalline TiO2-catalyzed one-pot synthesis of 3-[(piperidin-1-yl)phenylmethyl]- and 3-[(morpholin-4-yl)phenylmethyl]-4-hydroxycoumarins has been developed via three-component Mannich type condensation of 4-hydroxycoumarin with aromatic aldehydes and secondary amines (piperidine or morpholine) in ethanol at room temperature. The catalyst can be easily recovered and reused with almost the same catalytic activity. The proposed method is advantageous due to its simplicity, short reaction time, catalyst reusability, good to excellent yield, and clean and easy work-up.
    Russian Journal of Organic Chemistry 02/2015; 51(1):69-73. DOI:10.1134/S107042801501011X · 0.68 Impact Factor
  • Synlett 02/2015; 26(04). DOI:10.1055/s-0034-1379878 · 2.46 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: A new mesoporous Cu-MPTA-1 nanocatalyst has been synthesized via a simple and facile in situ radical polymerization of triallylamine in the presence of an organic-organic self-assembly of anionic surfactant SDS, followed by grafting of Cu(II) at room temperature under an inert atmosphere. This nanomaterial has been characterized by elemental analysis, powder X-ray diffraction (XRD), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FT-IR), UV-vis diffuse reflectance spectroscopy (DRS), thermogravimetric analysis (TGA), N2 adsorption-desorption studies, X-ray photoelectron spectroscopy (XPS) and EPR spectroscopy. Cu-MPTA-1 acts as an efficient heterogeneous nanocatalyst exhibiting a high catalytic activity for N-arylation and S-arylation reactions using water as a green solvent and also exhibits an excellent catalytic activity for the one-pot synthesis of propargylamines via a three component coupling of an alkyne, an amine and an aldehyde at room temperature. Moreover, the catalyst is easily recoverable and can be reused six times without an appreciable loss of catalytic activity in the three component coupling reaction. The highly dispersed Cu(II) sites in the Cu-grafted mesoporous polymer could be responsible for the observed high activities of the Cu-MPTA-1 catalyst in the coupling reactions. No evidence of leached Cu from the catalyst during the course of the reaction has been observed, suggesting true heterogeneity in the catalytic process.
    Catalysis Science & Technology 01/2013; 3(12):3303. DOI:10.1039/c3cy00600j · 4.76 Impact Factor

Full-text

Download
396 Downloads
Available from
May 26, 2014