Radical hydrotrifluoromethylation of ynamides: a route toward β-CF₃enamides

Abstract

We reported here a radical hydrotrifluoromethylation of ynamides to provide an alternative route to β-CF3 enamines. By the use of PhICF3Cl as the CF3 reagent and DMF as the H-donor,...

Catalytic intermolecular hydrofunctionalizations of ynamides

“…In 2022, Wang and co-workers reported an interesting radical hydrotrifluoromethylation of ynamides, which enabled a rapid access to β-CF 3 enamides (Scheme 26). 53 Using PhICF 3 Cl as the trifluoromethyl source and N , N -dimethylformamide (DMF) as the hydrogen donor, the transformation took place smoothly at room temperature in the presence of NaH. A wide variety of ynamides, regardless of their electronic properties, were all compatible with this approach.…”

Copper-Catalyzed 1,2-Difunctionalization Trifluoromethylamidation of Alkynes Assisted by a Coordinating Group

“…Given the importance of such two types of subunits in drug screening, the development of modular assembly of CF 3 -containing enamide scaffolds with a broad substrate scope and good functionality tolerance is highly desired and appealing. Recently, tremendous progress on β-trifluoromethylation of enamides has been achieved for the synthesis of such compounds (Figure c, left) . However, the representative known synthetic strategies typically encounter hazardous and expensive reagents, tedious multiple synthesis and purification, and/or limited substrate scope.…”

Radical Thiocyano(Selenocyano)trifluoromethylations of Alkenes on Water

“…In our ongoing research, we tried the application of PhICF 3 Cl in the thiocyanotrifluoromethylation reaction of olefins. According to previous work, CF 3 radical could be smoothly released from PhICF 3 Cl in the presence of a reductant [7e] . As such, we envisioned a radical thiocyanotrifluoromethylation of alkenes by the use of a SCN salt as the thiocyanating reagent without additional reductant.…”