RESUMO
A chemo-, regio-, and stereoselective reaction of trifluoromethyl enones, phenylsilane, and phosphine oxides through a sequential hydrodefluorination and defluorophosphorylation relay is developed for the synthesis of distinctive gem-fluorophosphine alkenes. This multicomponent reaction occurred under transition-metal-free conditions with good functional group tolerance. Moreover, the preinstalled carbonyl auxiliary is important for tuning the reactivity of ß-trifluoromethyl enones, thereby enabling controllable and selective functionalization of two fluorine atoms in trifluoromethylated enones.
RESUMO
An unprecedented defluorocyclization of perfluorobutyl tetralones with Na2S·9H2O was developed for the synthesis of trifluoromethyl 1,2-dithioles, which provided chemists novel access to biologically and pharmaceutically relevant organofluorides. Successive C(sp3)-F bond functionalization at the perfluoroalkyl chain is vital for the formation of four C-H/C-S/S-S bonds and a five-membered S-heterocycle assembly. Cheap, weakly toxic, and odorless inorganic sulfide Na2S·9H2O acts as both a disulfurating precursor and a hydrodefluorinating reagent in this tandem multi-bond-interconverting reaction.
Assuntos
TetralonasRESUMO
A modular multicomponent reaction of readily available fluoroalkyl alkenes, amidines, ammonium carbonate, and water was developed for the facile construction of ß-fluoroalkylated aminovinyl ketones, which provided chemists a novel access to value-added organofluorine compounds. The reaction proceeded regio-/stereoselectively under mild conditions and exhibited good functional group tolerance. Cheap, stable, and low-toxic inorganic salt (NH4)2CO3 was first found to act as both a nitrogen source and a carbonyl equivalent in the multi-bond-forming process.
