We described a trifluoromethylation of alkenes using PhICF3Cl as bifunctional reagent. Chlorotrifluoromethylated products were obtained when nonconjugated alkenes were treated with PhICF3Cl in 1,4-dioxane at 60 °C, while vinyl C–H trifluoromethylated products were obtained by further elimination of hydrochloride in the case of those conjugated alkene substrates in DMF. Broad substrate scope, especially including complex alkenes bearing biological active motifs, suggests that this mild reaction is feasible for late-stage modification in drug discovery.

Reassembly and functionalization of N-CF3 pyridinium salts is reported. The cascade is initiated by hydrolytic ring-opening of N-CF3 pyridinium salts, followed by defluorination, intramolecular nucleophilic addition, intermolecular nucleophilic substitution, and...

A new bicyclization of 4-cyano-1,2-diketones with amidines is reported for the construction of tetrahydro-5H-imidazo­[4,5-b]­pyridin-5-ones. The tandem reaction is proposed to involve the double condensation–cyclization of diketone with amidine, an α-ketol like rearrangement, the hydrolysis of nitrile followed by intramolecular nucleophilic addition, and the elimination of water. Features of the bicyclization method include high yields, good functional group tolerance, and mild reaction conditions.