An in-mediated tandem reaction of aldehydes with 3-bromo-1-propyne to produce 1-substituted-3-methylene-5-yn-1-ol compounds

A one-pot reaction for the synthesis of 1-substituted-3-methylene-5-yn-1-ol compounds from In-mediated propargylation of aldehydes with 3-bromo-1-propyne was reported. Our studies showed that the propargylic alcohol formed in the reaction was selectively subjected to further propargylation of the triple bond to afford the Markovnikov addition products in a regiospecific fashion.