Highly selective formation of propargyl- and allenyltrichlorosilanes and their regiospecific addition to various types of aldehydes: preparation of both allenic and homopropargylic alcohols

The highly selective preparation of propargyl- and allenyltrichlorosilanes via metal-catalyzed silylation of propargyl chloride has been developed. These trichlorosilyl nucleophiles were then shown to add to various types of aldehydes to afford the corresponding allenic and homopropargylic alcohols, respectively, in high yields with complete regiospecificity. Remarkably, these carbon–carbon bond-forming reactions simply proceeded in N,N-dimethylformamide (DMF) without using any metal catalysts.