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Synthesis 2011(23): 3915-3924  
DOI: 10.1055/s-0030-1260236
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Copper Nanoparticle-Doped Silica Cuprous Sulfate as a Highly Efficient and Reusable Heterogeneous Catalysis for N-Arylation of Nucleobases and N-Heterocyclic Compounds

Mohammad Navid Soltani Rad*a, Somayeh Behrouz*a, Mohammad Mahdi Doroodmandb,c, Noushin Moghtaderia
a Department of Chemistry, Shiraz University of Technology, Shiraz 71555-313, Iran
Fax: +98(711)7354520; e-Mail: soltani@sutech.ac.ir; e-Mail: behrouz@sutech.ac.ir;
b Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran
c Nanotechnology Research Institute, Shiraz University, Shiraz, Iran
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Publikationsverlauf

Received 28 July 2011
Publikationsdatum:
21. September 2011 (online)

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Abstract

A facile and simple protocol for Ullmann-type N-arylation of nucleobases with aryl halides is described using copper nanoparticle-doped silica cuprous sulfate (CN-DSCS) as a new and efficient heterogeneous catalysis. In this method, treatment of various nucleobases and aryl halides in the presence of DBU and CN-DSCS in refluxing DMF furnishes the corresponding N-aryl adducts in reasonable to good yields. The CN-DSCS was fully characterized by different microscopic, spectroscopic and physical techniques, including scanning electron microscopy (SEM), transmission electron microscopy (TEM), atomic force microscopy (AFM), X-ray diffraction (XRD), inductively coupled plasma (ICP) analysis, thermogravimetric analysis (TGA), and FT-IR. The CN-DSCS was proved to be a chemically and thermally stable, cheap, and environmentally compatible heterogeneous nanocatalyst that can be reused for many consecutive experiments without any considerable decrease in its reactivity.

Key words

CN-DSCS - heterogeneous catalysis - Ullmann-type reaction - N-arylation - nucleobase