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Directed Palladium Catalyzed C-H (Ethoxycarbonyl)difluoromethylthiolation Reactions. 2022
Floriane Doche, and
Julien Escudero, and
Fabien Petit-Cancelier, and
Heng-Ying Xiong, and
Samuel Couve-Bonnaire, and
Davide Audisio, and
Thomas Poisson, and
Tatiana Besset
Normandie Univ., INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000, Rouen, France).
The unprecedented Pd-catalyzed (ethoxycarbonyl)difluoromethylthiolation reaction of various unsaturated derivatives was studied. In the presence of the (ethoxycarbonyl)difluoromethylsulfenamide reagent I and under mild reaction conditions (60 °C), both 2-(hetero)aryl and 2-(α-aryl-vinyl)pyridine derivatives were smoothly functionalized with this methodology (37 examples, up to 87 % yield). Moreover, the synthetic interest of this fluorinated moiety was further showcased by its conversion into various original fluorinated residues. Finally, a plausible mechanism for this transformation was suggested.
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