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

Abstract : 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 CS-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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Submitted on : Tuesday, November 26, 2019 - 9:58:15 AM
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Amal Benzai, Xinzhe Shi, Fazia Derridj, Thierry Roisnel, Henri Doucet, et al.. Late-Stage Diversification of Imidazole-Based Pharmaceuticals through Pd-Catalyzed Regioselective C-H Bond Arylations. Journal of Organic Chemistry, American Chemical Society, 2019, 84 (20), pp.13135-13143. ⟨10.1021/acs.joc.9b01469⟩. ⟨hal-02359968⟩

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