Sulfonium Salt-Mediated Deoxyfluorination of Alcohols

The deoxyfluorination reaction has established itself as the most efficient methodology for direct fluorination, offering straightforward access to fluorinated compounds. In recent years, a number of deoxyfluorination reactions employing diverse fluorinating reagents and activating groups have been reported. Herein, we have developed a strategy for the rapid and mild sulfonium salt-mediated deoxyfluorination of alcohols without requiring preactivation. This innovative strategy demonstrates remarkable substrate versatility across tertiary, secondary, and primary alcohol substrates while maintaining exceptional functional group tolerance. Notably, we have successfully extended this strategy to complex natural molecules containing hydroxyl groups and established its viability for deoxyfluorination modifications. Combined control experiments and DFT calculations provide insights into the reaction pathway and the crucial role of the sulfonium salt in the reaction process.