Light-Mediated Sulfur–Boron Exchange
Liubov I. Panferova, Alexander D. Dilman
Abstract
Interaction of sulfides bearing a tetrafluoropyridinyl group with bis(catecholato)diboron followed by treatment with pinacol and triethylamine affording pinacol boronic esters is described. The reaction is promoted by an organic photocatalyst (3DPA2FBN) under irradiation with 400 nm light, and works with primary, secondary, and tertiary sulfides. The electron depleting character of the fluorinated pyridine fragment plays an important role in generating alkyl radicals.
Topics & Concepts
ChemistryPinacolTriethylamineBoronSulfurAlkylPyridineRadicalPrimary (astronomy)PhotochemistryPhotocatalysisOrganic chemistryMedicinal chemistryCatalysisPhysicsAstronomyRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods