Pentafluorohalobenzene (C6F5X) as Iodine or Bromine Transfer Reagents for Synthesis of Disubstituted Pyridines

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We report pentafluorohalobenzene (C 6 F 5 I and C 6 F 5 Br) as an iodine or bromine transfer reagent for the generation of both electron-rich and electron-poor (hetero)aryl iodides and bromides with excellent chemo/regio selectivity in up to 95% yields. Continuous flow synthesis proved to be advantageous for this transformation. The iodine or bromine transfer occurs through treatment with in situ-generated (hetero)aryl Grignard reagents derived from aryl halides with C 6 F 5 I or C 6 F 5 Br. The resulting iodo- and chloro/bromo-pyridines were further transformed into bis-substituted pyridines through subsequent chemoselective coupling reactions.

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