Efficient Synthesis of Diaryl Sulfides via Three Component Cross Coupling

Diaryl sulfides are found in drugs and natural products, yet their synthesis traditionally requires metal-catalyzed cross-coupling reactions, high temperatures, and the use of the air-sensitive and extremely odorous thiophenols.A novel transition-metal-free strategy for the synthesis of unsymmetric diaryl sulfides via a three-component cross-coupling of polyfluoroarenes, diaryliodide salts and potassium thioacetate is reported.This approach enables the formation of a diverse array of unsymmetric diaryl thioethers through two successive electrophilic substitution reactions involving commercially available potassium thioacetate and two electron-deficient aromatic hydrocarbons, demonstrating broad substrate scope and functional group compatibility.Additionally, this strategy facilitates the synthesis of sulfones and sulfoxides via a one-pot oxidation reaction, thereby extending its applicability.Gram-scale reactions and derivatization experiments have shown excellent results, further proving the potential application value of this reaction.Mechanistic insights were elucidated through control, radical inhibition and intermediate capture experiments.