Copper- and palladium-catalyzed intramolecular aryl guanidinylation: an efficient method for the synthesis of 2-aminobenzimidazoles |
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Authors: | Evindar Ghotas Batey Robert A |
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Affiliation: | Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada. |
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Abstract: | [reaction: see text] The formation of 2-aminobenzimidazoles via intramolecular C[bond]N formation between an aryl halide and a guanidine moiety can be achieved using either copper or palladium catalysis. Inexpensive copper salts such as CuI are generally superior to the use of palladium catalysts. Regioselective cyclizations, where R(3) = H, can be achieved in high yield under CuI/1,10-phenanthroline-catalyzed conditions, whereas palladium catalysis results in the formation of regioisomeric products. |
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