Journal
TETRAHEDRON
Volume 65, Issue 4, Pages 855-861Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.11.036
Keywords
Arylation; Nucleophilic aromatic substitution; Pyrazole; Imidazole; Pyrrole; Copper catalysis
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Arylation reactions of NH-heterocycles [specifically, pyrazole, 3-(trifluoromethyl)pyrazole, imidazole and pyrrole] with 2,4-difluoroiodobenzene in the absence and presence of copper catalysis are described. The combination of fluor and iodo substituents in the same aryl substrate has facilitated both SNAr reactions at the C-F bonds and copper-catalysed Ullmann-type coupling reactions at the C-I bond. Products arising from regioselective reactions and multiple substitutions have been isolated, providing a range of new N-arylated pyrazole, imidazole and pyrrole derivatives. (C) 2008 Elsevier Ltd. All rights reserved.
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