Sulfenylation of cyclohexenone esters by trifluoromethane-sulfenyl chloride

Synthetic Methods for Compounds Having CF3–S Units on Carbon by Trifluoromethylation, Trifluoromethylthiolation, Triflylation, and Related Reactions

“…The reactions of various carbonyl compounds with CF 3 SCl were reported in the last century (eq a, Scheme ). − Under the conditions with or without a base, the corresponding α-SCF 3 carbonyl compounds were obtained in good yields. Sometimes the bis­(trifluoromethylthio)-substituted products were produced. ,,, In 2000, Munavalli utilized N -(trifluoromethylthio)­phthalimide as the trifluoromethanesulfenylation reagent for the preparation of α-SCF 3 carbonyl compounds (eq b, Scheme ) .…”

Direct Trifluoromethylthiolation Reactions: The “Renaissance” of an Old Concept

“…In addition to aryl trifluoromethyl sulfides, synthesis of α‐trifluoromethanesulfenyl‐substituted ketones received attention (Scheme 10). It was reported that CF 3 SCl reacts with enolizable ketones,35 malonate derivatives,35,36 β‐keto esters,35,36 β‐diketones,37 and cyclohexenone esters 38…”

Synthesis of Alpha‐trifluoromethylthio Carbonyl Compounds: A Survey of the Methods for the Direct Introduction of the SCF3 Group on to Organic Molecules

“…[46] Few years later also the a-trifuoromethylthiolation of ketones, [47] cyclic b-diketones, [48] b-keto acids [49] and cyclohexanone esters [50] performed with CF 3 SCl were reported in good yields (Scheme 31). In this field, the first example of SCF 3 electrophilics ubstitution was reportedb yH aas in 1980; diethyl malonate reacts with the toxic electrophilic CF 3 SCl to form mono-and di-substituted products.…”

“…In this field, the first example of SCF 3 electrophilics ubstitution was reportedb yH aas in 1980; diethyl malonate reacts with the toxic electrophilic CF 3 SCl to form mono-and di-substituted products. [46] Few years later also the a-trifuoromethylthiolation of ketones, [47] cyclic b-diketones, [48] b-keto acids [49] and cyclohexanone esters [50] performed with CF 3 SCl were reported in good yields (Scheme 31).…”