ChemInform Abstract: Palladium Catalyzed Aryl(alkyl)thiolation of Unactivated Arenes.

Abstract

A general palladium‐catalyzed aryl(alkyl)thiolation of various substituted unactivated arenes is accomplished for the synthesis of diverse unsymmetrical diaryl(alkyl) sulfides employing an electrophilic sulfur reagent derived from succinimide.

Recent developments in palladium-catalyzed C–S bond formation

“…For instance, Anbarasan and co-workers discovered a palladium-catalyzed aryl(alkyl)thiolation of arenes (1) with electrophilic sulfenylating reagents (2) for the direct construction of diverse unsymmetrical diaryl or arylalkyl sulfides (3) in good yields with highly selectivity (Scheme 1). 21 (trifluoroacetic acid) as the solvent were essential for this protocol. Moreover, under the optimized arylthiolation conditions, various aryl, alkyl, and heteroaryl substituted sulfenylating reagents 2 were confirmed as good coupling partners.…”

“…31 It was found that Pd(MeCN) 2 Cl 2 could efficiently catalyze this sulfenylation protocol in the absence of phosphine ligands or any other additives. Under optimized conditions, arenes bearing a direction group were allowed to react with various N-arylthiobenzamides, affording the corresponding aryl thioethers (21) or dithioethers (22) in moderate to good yields. A variety of functional groups, such as cyano, trifluoromethyl, methoxyl, and ester groups were perfectly tolerated.…”