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A metal-free and photo-free method for the perfluoroalkylative pyridylation of alkenes has been developed via a combination of computational and experimental studies. Density functional theory calculations and control experiments indicate that the homolysis of R f -X (X = Br, I) bonds by the 4-cyanopyridine-boryl radicals in situ generated from 4-cyanopyridine and B 2 pin 2 is the key step. Sequential addition of R f radicals to alkenes and the selective cross-coupling of the resulting alkyl radicals and 4-cyanopyridine-boryl radicals gives alkene difunctionalization products with a quaternary carbon center. This method exhibits a broad substrate scope and good functional group compatibility.

Perfluoroalkylative pyridylation of alkenesvia4-cyanopyridine-boryl radicals