Progress of the Research on the Lewis/Bronsted Acid-Catalyzed Nucleophilic Substitution of Propargyl Alcohols

Lewis/Bronsted acid-catalyzed nucleophilic substitution of propargylic alcohols is very important in organic synthetic chemistry, which could be transformed into a variety of acyclic, carbocyclic and heterocyclic synthetic building blocks. A drawback of the traditional propargylation of Nicholas reaction is the generation of waste products resulting from displacement of the leaving group on treating with a catalyst and/or nucleophile. Therefore, the direct acid-catalyzed propargylation of propargylic alcohols is considered as a green method, which generated water as the only side product. In this review, the latest research progress on the Lewis and Bronsted acids catalyzed intermolecular and intramolecular propargylation of a variety of nucleophiles (NuH=C, N, O, S, I) with propargylic alcohols is presented. Finally, the problems and difficulties in research and application of propargylation of propargylic alcohols are discussed and then prospective is provided.