New stable reagents for the nucleophilic trifluoromethylation. Part 4: Trifluoromethylation of disulfides and diselenides with hemiaminals of trifluoroacetaldehyde

Strategies for nucleophilic, electrophilic, and radical trifluoromethylations

“…Afterwards, Langlois and coworkers developed stable hemiaminals of fluoral 23 and their silylated derivatives 24 as powerful trifluoromethylating agents towards non-enolisable carbonyl compounds, disulfides, and diselenides under activation by a stoichiometric strong base or catalytic fluoride anion such as CsF, and TBAT (Scheme 23). Fluoroform or more conveniently fluoral methyl hemiketal served as starting material for preparation of 23 and 24 [63][64][65][66].…”

Alkynyl trifluoromethyl selenide synthesis via oxidative trifluoromethylselenolation of terminal alkynes

“…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. [46][47][48][49][50][51][52] The organoselenium compounds also display significant potential as antioxidant, antitumor, antimicrobial, and antiviral agents. This probably because the starting materials and reagents are either highly toxic, unstable, commercially unavailable, or require elaborate preparative methods.…”

Selective oxidation and chlorination of trifluoromethylsulfide using trichloroisocyanuric acid in ionic liquid

“…There are many methods about the synthesis of aryltrifluoromethylsulfides [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33]. Thereinto, the reaction of aryl disulfide with trifluoromethyl bromide in the presence of sulfoxylate anion radical precursors developed by Wakselman et al [23,24] constitute an important method of synthesis.…”