Radical Substitution of Polyfluoroarenes and Heteroarenes Promoted by Photoredox Activation of Organozinc Iodides

Aromatic compounds interact with organozinc reagents under photoredox conditions, leading to the substitution products. The reaction is performed under blue light irradiation via in situ generated organozinc reagents (Barbier conditions), which are oxidized by the photocatalyst, followed by radical attack at the aromatic substrate. The method works with polyfluorinated arenes, 2-chlorobenzoxazoles, and 2-sulfonyl-substituted benzothiazole. image

Automated summary

Aromatic compounds undergo substitution reactions with organozinc reagents under photoredox conditions. The reaction occurs under blue light irradiation with in situ generated organozinc reagents (Barbier conditions), which are oxidized by the photocatalyst, followed by radical attack on the aromatic substrate. This method is effective for polyfluorinated arenes, 2-chlorobenzoxazoles, and 2-sulfonyl-substituted benzothiazole.