Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2006, Issue 6, Pages 1379-1382Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200500957
Keywords
C-C coupling; synthetic methods; regioselectivity; palladium; copper
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The first palladium- and copper-mediated C-2 arylations of thiazole, oxazole, N-methylimidazole and N-arylimidazoles, as well as of free (NH)-imidazole, -benzimidazole and -indole, with aryl iodides under ligandless and base-free conditions are described. Complete selectivity has been achieved under these unprecedented conditions, which allow the use of substrates containing base-sensitive groups, such the NH groups of imidazole, benzimidazole or indole, without their prior protection. No N-arylation products were detected in the arylation of free (NH)-imidazole, -benzimidazole and indole. (c) Wiley-VCH Verlag GmbH & Co.
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