Taming Brønsted Acid Reactivity: Nucleophilic Substitutionsof Propargylic Alcohols with N-Nucleophiles Mediated by Phosphorus-BasedBrønsted Acid Catalysts

摘要

The activity of diethyl phosphite and diphenyl phosphate in propargylation reactions with N-nucleophiles of varying basicity is presented. A careful choice of the reaction conditions minimized undesired rearrangements and arylation processes, typical side reactions with Brønsted acid catalysis. These systems are compatible with technical solvents and presence of air, and they are also applicable to C-, O-, and S-nucleophiles.