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Directed Palladium Catalyzed C−H (Ethoxycarbonyl)difluoromethylthiolation Reactions

Von Wiley-VCH zur Verfügung gestellt

The unprecedented construction of a C(sp2)-SCF2CO2Et bond was successfully achieved by Pd-catalyzed C−H bond activation. This robust protocol allowed the functionalization of a broad panel of aromatic and olefinic derivatives (37 examples, up to 87 % yield), a real advance as existing routes were restricted to the SCF3 and SCF2H residues. Post-functionalization reactions further illustrated the synthetic value of this fluorinated motif.


Abstract

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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