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Unusual Regioselective C-H Difluoroalkylation of Heteroarenes under Photoredox Catalysis.

Sudip LaruSourav GhoshalPranab SarkarAlakananda Hajra
Published in: Organic letters (2024)
We disclose a new general strategy for the site-selective difluoroalkylation of nonprefunctionalized heteroarenes, such as quinoxaline at the C-8 position, and benzothiadiazole, benzoxadiazole, and benzothiazole at the C-4 position via consecutive organophotoredox-catalyzed radical-radical cross-coupling and base-assisted hydrogen abstraction reactions. The current methodology represents a site-selective direct difluoroalkylative strategy to allow broad functional group tolerance and a wide substrate scope in good to excellent yields. Careful experimental investigations and detailed DFT calculations revealed the exact site-selectivity of the heteroarenes and a possible mechanistic pathway.
Keyphrases
  • density functional theory
  • visible light
  • molecular dynamics
  • molecular dynamics simulations
  • molecular docking
  • monte carlo