Aryl sulfonyl fluoride synthesis via palladium-catalyzed fluorosulfonylation of aryl thianthrenium salts

We developed an efficient palladium-catalyzed fluorosulfonylation reaction of aryl thianthrenium salts to smoothly prepare various aryl sulfonyl fluorides using cheap Na2S2O4 as a convenient sulfonyl source in combination with N-fluorobenzenesulfonimide (NFSI) as an ideal fluorine source under mild reduction conditions. A one-pot synthesis of aryl sulfonyl fluorides starting from various arenes was established as well without the need for separating aryl thianthrenium salts. The practicality of this protocol was demonstrated by gram-scale synthesis, derivatization reactions, and excellent yields.

Automated summary

We developed an efficient palladium-catalyzed fluorosulfonylation reaction using aryl thianthrenium salts, Na2S2O4, and NFSI to prepare aryl sulfonyl fluorides. This one-pot synthesis avoids the separation of aryl thianthrenium salts and has demonstrated practicality through gram-scale synthesis and high yields.