N‐Trifluoromethylthiophthalimide: A Stable Electrophilic SCF₃‐Reagent and its Application in the Catalytic Asymmetric Trifluoromethylsulfenylation

Abstract

Cinchona alkaloid catalysts in combination with air- and moisture-stable N-trifluoromethylthiophthalimide as electrophilic SCF3 source enabled the catalytic enantioselective trifluoromethylsulfenylation. Thus, a series of α-SCF3 esters that bear a quaternary carbon stereogenic center were obtained with excellent yield and enantioselectivity. Moreover, the products can be readily converted into valuable α-SCF3 β-hydroxyesters.

First and second generation of trifluoromethanesulfenamide reagent: A trifluoromethylthiolating comparison

“…More specifically, new electrophilic trifluoromethylthiolating reagents [24][25][26][27][28][29][30] were highly required to replace CF 3 SCl, the only reagent available until recently, but very toxic [31].…”

Alkynyl trifluoromethyl selenide synthesis via oxidative trifluoromethylselenolation of terminal alkynes

“…[1][2][3][4][5][6][7][8] Among such compounds trifluoromethyl thioethers have attracted a great deal of attention in the past years owing to their strong electron-withdrawing effects and high lipophilicity. [13][14][15][16][17][18] Recently, the development of new trifluoromethylthiolating reagents [19][20][21][22][23][24][25][26][27][28][29][30] and transitionmetal-catalyzed or -mediated trifluoromethylthiolation has found many applications for assembling aryl and alkyl trifluoromethyl thioethers. [13][14][15][16][17][18] Recently, the development of new trifluoromethylthiolating reagents [19][20][21][22][23][24][25][26][27][28][29][30] and transitionmetal-catalyzed or -mediated trifluoromethylthiolation has found many applications for assembling aryl and alkyl trifluoromethyl thioethers.…”

Direct Trifluoromethylthiolation and Perfluoroalkylthiolation of C(sp2)H Bonds with CF3SO2Na and RfSO2Na

“…[5] Since they are highly reactive and hard-to-handle gaseous chemicals,aseries of CF 3 S-based reagents,i ncluding quaternary ammonium Me 4 NSCF 3 , [6] metallic CuSCF 3 and AgSCF 3 , [7] and the shelf-stable chemicals 1a-f,h ave been developed for trifluoromethylthiolation ( Figure 1). [8][9][10][11][12][13] However,t hey have to be prepared by trifluoromethylthiolation or trifluoromethylation reactions,and could be very expansive.In2009, the group of Magnier reported aCF 3 SO 2 K-initiated trifluoromethylation reaction. As mall amount of trifluoromethylthiolation product was detected in the reaction mixture.…”