Palladium-Catalyzed Formation and Subsequent Transformations of Silicon-Fluorine Species from Acyl Fluorides

Ligand-controlled palladium-catalyzed reactions of acyl fluorides with hydrosilanes enables the selective generation and isolation of silicon-fluorine species, R3Si-F, which have typically been regarded as inert by-products in organosilicon chemistry. The formation of these silicon-fluorine compounds was confirmed by both 19F NMR and 29Si{1H} NMR spectroscopic analyses, and one of the isolated species, Ph3Si-F, was found to undergo a subsequent palladiumcatalyzed transformation via Si-F bond cleavage. These results demonstrate silicon-fluorine species as potential viable intermediates in palladium catalysis and expand the synthetic utility of acyl fluorides as versatile fluorine sources.