Synthetic Uses of Thio- and Selenoesters of Trifluoromethylated Acids. 1. Preparation of Trifluoromethyl Sulfides and Selenides
作者:Thierry Billard、Nicolas Roques、Bernard R. Langlois
DOI:10.1021/jo980649a
日期:1999.5.1
Trifluorothioacetates (CF3CO-S-R, from (CF3CO)(2)O and thiols) as well as trifluoromethanethio-or trifluoromethaneselenosulfonates (CF3SO2-Y-R; Y = S, Se; from CF3SO2Na, RYYR, and Br-2) can be formally decarbonylated or desulfonylated, respectively, provided that they are photolyzed at 40 degrees C in the presence of 1 equiv of the corresponding disulfide or diselenide. Trifluoromethyl sulfides or selenides are obtained, and the added disulfide (or diselenide) is recovered after reaction. In such a way, S-(trifluoromethyl)cysteine derivatives can be obtained.
Direct Perfluoroalkylthiolation of Few Chalcogenols
作者:Quentin Glenadel、Thierry Billard
DOI:10.1002/cjoc.201500913
日期:2016.5
Trifluoromethanesulfenamide reagent can react with alcohols, in basic conditions, or with thiols, in catalytic acid conditions, to afford the corresponding trifluoromethanesulfenates or trifluoromethyldisulfides. The use of higher homologs of this reagent leads to synthesis of the nearly unknown perfluoroalkanesulfenates and perfluoroalkyldisulfides.