Trifluoromethylsulfenylation of Masked Carbonyl Compounds

Deoxytrifluoromethylthiolation and Selenylation of Alcohols by Using Benzothiazolium Reagents

“…With the highest reported Hansch parameter (p = 1.44) and strong electron-withdrawing properties (Hammett parameters: s m = 0.40, s p = 0.50), the trifluoromethylthio (SCF 3 )g roup in particular has emergeda sapromising substituent in pharmaceuticals that counterintuitively combines significant polarity with high lipophilicity. [2,3] By contrast, nucleophilic trifluoromethylthiolation reactions are typicallyp erformed by using only ah andfulo f À SCF 3 sources, such as AgSCF 3 ,C uSCF 3 ,a nd [Me 4 N]SCF 3 . As demonstratedi na number of impressive contributions, reagents such as N-(trifluoromethylthio)phthalimide, [2(2-iodophenyl)propan-2-yl)oxy]-(trifluoromethyl)sulfane and Billard's trifluoromethyl sulfenamides have opened up new mild synthetic routes towards SCF 3 -substituted molecules that were not accessible by using the previously availablet oxic gases F 3 CSÀCl and F 3 CSÀSCF 3 .…”

N‐Trifluormethylthiophthalimid: ein stabiles, elektrophiles SCF3‐ Reagens und seine Anwendung in der katalytischen asymmetrischen Trifluormethylsulfenylierung

“…[5] Mehrere neue Ansätze zur Bildung von C(sp 2 Aryl )-SCF 3 -Bindungen unter milden Reaktionsbedingungen wurden entwickelt, welche nukleophile Trifluormethylsulfenylierungsreagentien wie CuSCF 3 verwenden. Zu Beginn unserer Arbeit an einer asymmetrischen Trifluormethylsulfenylierung waren nur zwei weitere elektrophile SCF 3 -Quellen bekannt: Munavallis N-Trifluormethylthiophthalimid [8] 1 und Billards Trifluormethansulfanylamide [9] 2 (Abbildung 1 b). Dies ist nicht verwunderlich, da sowohl Synthese als auch Stabilität der elektrophilen SCF 3 -Reagentien problematisch sein kann.…”

Transition‐Metal‐Free Trifluoromethylthiolation of N‐Heteroarenes

“…To address the demands for synthetic procedures made by the pharmaceutical and agrochemical fields, we envisaged the development of a transition metal‐free method for trifluoromethylthiolation that is robust, operationally simple, and generally applicable to pyrroles, indoles, and related heteroarenes. We chose compound 5 (Figure 2) as the electrophilic reagent,16 due to its high stability and ease of synthesis, as reported by Rueping and co‐workers 8d. Additionally, to date, this reagent has not been applied in the CH functionalization of heteroarenes.…”