Photocatalytic Sulfonyl Fluorination of Alkyl Organoboron Substrates.

Abstract

Sulfonyl fluorides are highly versatile molecules for click chemistry that have found applications in many areas of chemistry and biology. Recent chemical approaches have focused on the synthesis of alkyl sulfonyl fluorides from readily available starting materials. Here, we report a photocatalytic synthesis of alkyl sulfonyl fluorides from organotrifluoroborates and boronic acid pinacol esters, which are building blocks commonly employed by medicinal chemists in the synthesis of bioactive molecules. Steady-state and time-resolved spectroscopy have confirmed that the absorption of photons by the acridinium catalysts leads to the oxidation of the organotrifluoroborate substrates. The reaction exhibits broad functional group tolerance, which can be attributed to the mild activation with visible light. Importantly, this general approach provides easy access to primary, secondary, and tertiary alkyl sulfonyl fluorides.