An Electrophilic Hypervalent Iodine Reagent for Trifluoromethylthiolation

Abstract

Sulfur and friends: A new electrophilic hypervalent iodine reagent 1 has been developed for direct trifluoromethylthiolation. A variety of nucleophiles, including β‐ketoesters, aldehydes, amides, aryl or vinyl boronic acids, and alkynes, reacted with 1 under mild conditions to give the corresponding trifluoromethylthiolated compounds in good to excellent yields.

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.…”

“…[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. These includes oxidative trifluoromethylthiolation of terminal alkynes with CF 3 SiMe 3 , and elemental sulphur 42 or later with AgSCF 3 , 43 copper-catalyzed trifluoromethylthiolation of terminal alkynes with a novel thioperoxy reagent, 25 base-catalyzed trifluoromethylthiolation of terminal alkynes with a trifluoromethanesulfenamide reagent, 44 and bismuth(III)promoted trifluoromethylthiolation of trimethyl(alkynyl)silane with trifluoromethanesulfanylamide reagent. These includes oxidative trifluoromethylthiolation of terminal alkynes with CF 3 SiMe 3 , and elemental sulphur 42 or later with AgSCF 3 , 43 copper-catalyzed trifluoromethylthiolation of terminal alkynes with a novel thioperoxy reagent, 25 base-catalyzed trifluoromethylthiolation of terminal alkynes with a trifluoromethanesulfenamide reagent, 44 and bismuth(III)promoted trifluoromethylthiolation of trimethyl(alkynyl)silane with trifluoromethanesulfanylamide reagent.…”

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

“…[43] Using Lu and Shen's reagent 8 as SCF 3 transfer, [44] a-SCF 3substituted indanone-derived b-ketoesters were obtained in high yields and with up to > 99 %e nantiomeric excess. [43] Using Lu and Shen's reagent 8 as SCF 3 transfer, [44] a-SCF 3substituted indanone-derived b-ketoesters were obtained in high yields and with up to > 99 %e nantiomeric excess.…”