Suzuki–Miyaura Cross‐Coupling of Potassium Organoborates with 6‐Sulfonate Benzimidazoles Using Microwave Irradiation |
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Authors: | Prashi Jain Shuyan Yi Patrick Thomas Flaherty |
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Institution: | School of Pharmacy, Division of Medicinal Chemistry, Graduate School of Pharmaceutical Sciences, Duquesne University, , Pittsburgh, Pennsylvania, United States |
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Abstract: | This article focuses on the utility of organotrifluoroborate salts as coupling partners for Suzuki–Miyaura cross‐coupling with 4‐nitro‐6‐triflyl benzimidazoles using microwave irradiation. The C–C bond formation at the 6‐position of the electron‐rich 1‐,4‐,6‐trisubstituted benzimidazole core is challenging and was not achievable via Kumada, Negishi, Stille, or Heck coupling strategies. Yields of 37–70% could be obtained via palladium coupling strategies utilizing potassium benzyl trifluoroborates as the organometallic coupling partner. |
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