TBAF-Catalysed Facile Synthesis of Unsymmetrical Diaryl Thioethers via Mild S_NAr Reactions

Abstract

By using tetrabutylammonium fluoride as the catalyst, the synthesis of unsymmetrical diaryl thioethers could be easily achieved in high yields via a mild nucleopilic aromatic substitution reaction of aryl fluorides and phenylthiotrimethylsilane.

Dechalcogenization of Aryl Dichalcogenides to Synthesize Aryl Chalcogenides via Copper Catalysis

“…For instance (Figure ), aryl chalcogenides could be found in 5-lipoxygenase inhibitor AZD4407, antitumor drug Axitinib, and organic electronic material triselenasumanene . In view of their significance in such broad fields, various methods for synthesizing aryl sulfides have been developed, mainly including the following three strategies: (a) transition-metal-catalyzed coupling of aryl halides, arylboronic acids, or other metal reagents with thiols, disulfides, or functionalized sulfurs (Scheme a), in which several of these protocols use precious metal, prefunctionalized sulfur, and sensitive metallic reagent; (b) metal-catalyzed functionalization of C–H bonds, for which the application and substrate scope of some have been restricted for the difficulty of directing group escaping (Scheme b); and (c) nucleophilic substitution (S N Ar) reactions, which are exclusively applicable for electrophilic aromatics (Scheme c). Despite that significant progress has been made in aryl sulfides synthesis, the longstanding issues existed in the above-mentioned strategies should not be overlooked; thus, alternatives are in great need.…”