pubs.acs.org/joc
chemistry.5 Due to the economic attractivness of copper6
CuI Nanoparticles for C-N and C-O Cross
Coupling of Heterocyclic Amines and Phenols with
Chlorobenzenes
and by using some special ligands such as N,N- and N,
O-bidentate compounds, many CuI-catalyzed C-N,7
C-O,8 C-S,9 and C-C10 bond formation reactions have
led to a resurgence of interest in carbon-heteroatom cou-
pling reactions, and their applications seem to be of more
and more importance.11,12 Despite significant progress in the
Cu-catalyzed N/O-arylation with aryl halides, only a few
reports have appeared describing the couplings of imidazoles
and/or phenols with aryl chlorides/bromides or of functional
substrates or of hindered substrates13,14 without the recovery
of catalyst. Therefore, it is important to develop more simple
and efficient catalytic systems for the cross-coupling meth-
odology with an ability to utilize inexpensive aryl chlorides15
with reusability of catalyst, and some of these have emanated
from our own laboratories.16
B. Sreedhar,* R. Arundhathi, P. Linga Reddy, and
M. Lakshmi Kantam
Indian Institute of Chemical Technology, Hyderabad 500007,
India
Received July 10, 2009
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Employing CuI nanoparticles as an efficient catalyst for
the cross-coupling reactions of various N/O nucleophilic
reagents with aryl chlorides could be successfully carried
out under mild conditions in the absence of both the
ligands and strong bases. A variety of products including
N-arylimidazoles and aryl ethers were synthesized in
good to excellent yields.
N-Arylimidazoles and aryl ethers are valuable compounds
widely employed in organic synthesis, pharmaceutical, and
biological areas.1 The development of a mild and highly
efficient method for synthesis of N-arylazoles over classical
Ullman type,2 or nucleophilic aromatic substitution
reactions,3 or coupling with organometallic reagents4
has recently gained considerable attention in synthetic
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DOI: 10.1021/jo901462g
r
Published on Web 09/22/2009
J. Org. Chem. 2009, 74, 7951–7954 7951
2009 American Chemical Society