A Simple, Fast and Chemoselective Method for the Preparation of Arylthiols

Abstract

C h e m o s e l e c t i v e P r e p a r a t i o n o f A r y l t h i o l sAbstract: An efficient and convenient method for the synthesis of arylthiols by reaction of sulfonyl chlorides with triphenylphosphine in toluene is reported.

Synthesis and structure–activity relationship of aminoarylthiazole derivatives as correctors of the chloride transport defect in cystic fibrosis

“…The compound N, 4-bis (3-(methylthio) phenyl) thiazol-2-amine (4b) was prepared starting from the reduction of 3-acetylbenzene-1-sulfonyl chloride to 1-(3-mercaptophenyl) ethanone according to the published procedure [20]. Afterwards, the ketone was methylated with iodomethane at thiol portion, brominated with NBS and conjugated with 1-(3-(methylthio) phenyl) thiourea a.…”

“…The compound 14e was synthetized from a particular Nsubstituted thiourea e obtained from the reaction of 2-ethyl 3-methyl thioaniline with benzoyl isothiocyanate followed by saponification to remove the benzoyl group as previously described [15]. The 2-ethyl 3-methyl thioaniline derived from the reaction of 4-ethylnitrobenzene with chlorosulfonic acid and subsequent reduction with tryphenylphosphine [20,21]. The nitroderivative was indeed methylated on the thiol group and subsequently reduced to aniline with Zn/saturated NH 4 Cl [22] (Scheme 2).…”

Redox-Click Chemistry for Disulfide Formation from Thiols

“…Therefore, SO2F2 cannot be reduced by most of the known reductant because of the high kinetic barrier. For example, triphenylphosphine, a widely used reductant (36), can be oxidized by sulfuryl chloride rapidly at r.t (37), but the reaction between sulfuryl fluoride and triphenylphosphine is very slow even at elevated temperature (calculated barrier, 43.5 kcal/mol; Fig 2B) (38).…”

ADDP facilitates C–S bond formation from sulfonyl chlorides with alcohols

“…14 A method for making arylthiols by reducing aryl sulfonyl chloride with PPh 3 and H 2 O was published by Krishnacharya G. Akamanchi's group in 2009. 15 This inspired us to investigate whether sulfonyl chlorides can be used as a sulfur source with alcohols instead of harmful alkylating reagents. In Liu's work, arylsulfonyl chlorides have been used extensively in the synthesis of diaryl thioethers.…”