Cobalt-catalyzed arylation of azole heteroarenes via direct C-H bond functionalization |
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Authors: | Sezen Bengü Sames Dalibor |
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Affiliation: | Department of Chemistry, Columbia University, 3000 Broadway, New York, New York 10027, USA. |
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Abstract: | [reaction: see text] We herein report a new cobalt-catalyzed method for arylation of azole heteroarenes, including thiazole, oxazole, imidazole, benzothiazole, benzoxazole, and benzimidazole. The direct arylation of thiazole and oxazole was achieved both with iodo- and bromoarenes as the aryl donors in the presence of cobalt catalyst [Co(OAc)(2)/IMes] and cesium carbonate, while imidazole required the use of zinc oxide as the base. A complete reversal of arylation from C-5 to C-2 was accomplished using the bimetallic Co/Cu/IMes system. A direct comparison of the new cobalt method and the previously developed palladium protocol revealed significant differences, in terms of both chemical yield and selectivity. |
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