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Late-Stage Diversification of Imidazole-Based Pharmaceuticals through Pd-Catalyzed Regioselective C–H Bond Arylations

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posted on 01.08.2019, 17:48 by Amal Benzai, Xinzhe Shi, Fazia Derridj, Thierry Roisnel, Henri Doucet, Jean-François Soulé
Palladium-catalyzed C–H bond arylation of imidazoles has been applied to pharmaceuticals such as Bifonazole, Climbazole, and Prochloraz. In the presence of phosphine-free Pd­(OAc)2 catalyst, aryl bromides are efficiently coupled at the C5-position of the imidazole units, which are widely decorated. Under these conditions, only C–H bond arylation reaction occurred without affecting the integrity of chemical structure of the imidazole-based pharmaceuticals. Moreover, with Bifonazole Pd-catalyzed C–H bond diarylation at the C2- and C5-positions of imidazole unit has also been performed.

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