Semi-heterogeneous photocatalytic fluoroalkylation-distal functionalization of unactivated alkenes with RFSO2Na under air atmosphere

Abstract

An efficient and eco-friendly heterogeneous photocatalytic system for the fluoroalkylation-distal heteroaryl, formyl and imino migration reactions has been developed by employing K-modified carbon nitride (CN-K) as a recyclable, nontoxic and heavy metal-free photocatalyst. This visible light-mediated protocol, utilizing air as the most “green” oxidant with R_FSO₂Na as bench-stable, inexpensive, low toxic and easy-to-handle fluoroalkyl sources, allows for the rapid and flexible construction of diverse valuable fluoroalkyl functionalized aldehydes, imines and heteroarenes. Active species trapping experiments and ESR-spin trapping study reveal that superoxide radicals, photogenerated electrons and holes all play an important role in the reaction process.