A general palladium-catalyzed aryl(alkyl)thiolation of various substituted unactivated arenes is accomplished for the synthesis of diverse unsymmetrical diaryl(alkyl) sulfides in good yield employing electrophilic sulfur reagent 6 derived from succinimide. The developed strategy was coupled with intramolecular arylation of a C-H bond to afford dibenzothiphene derivatives, an important moiety in material science as organic semiconductors.
An efficient regioselective difunctionalization of alkenes via trifluoromethylthiolation has been accomplished employing diaryl diselenide and AgSCF3 in the presence of BF3·OEt2.
Thed irect andr egioselective copper/S-Phos-catalyzedt rifluoromethylthiolation of symmetrical andu nsymmetrical di(hetero)aryl-l 3 -iodanes has been accomplishedf or the synthesiso fv arious (hetero)aryl trifluoromethyl sulfides employingr eadily accessible silver trifluoromethylthiolate (AgSCF 3 ) as nucleophilict rifluoromethylthiolating reagent. Thed eveloped transformation tolerates various functional groups like nitrile, enolizable ketone,e ster, nitro andf ree carboxylic acid. Interestingly,t he formal trifluoromethylthiolation of arenes was also achieved through integration of the synthesis of diaryl-l 3 -iodanes from arenes with the trifluorome-thylthiolation. Mechanistic investigations did not favor the radical formation and SET pathway.B ased on the variable temperature 19 FNMR spectroscopy, isolation of the most relevant catalytic intermediate, and stoichiometrics tudies supported the Cu(I)/ Cu(III) catalytic cycle,w herein the oxidative addition of diaryl-l 3 -iodanesw as assisted by the silver salt.
An efficient and general trifluoromethylthiolation of silylenol ethers and β‐naphthols have been accomplished employing the combination of diethylaminosulfur trifluoride (DAST) and (trifluoromethyl)trimethylsilane (CF3TMS) as source of electrophilic trifluoromethylthio moiety for the synthesis of α‐trifluoromethylthiolated carbonyl compounds and β‐naphthols in good yields. Important features of this method include wide functional group tolerance and use of readily available DAST/CF3TMS. Potential of the methodology was demonstrated via the synthesis of α‐trifluoromethylthiolated (+)‐4‐cholesten‐3‐one and naphthoquinone.magnified image
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.
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