Visible-Light-Induced Stereoselective Radical trans-Iodoalkylation of Terminal Alkyne with Iodoform.

ABSTRACT

We describe herein a novel stereoselective trans-iodoalkylation protocol by using three components of nucleophilic dicarbonyl compounds, iodoform and terminal alkynes. The generation of tertiary carbon radical species under mild reaction conditions allows this radical addition and stereoselective iodine atom transfer sequence with terminal alkyne to access highly synthetic applicable disubstituted vinyl iodide. The synthetic application of the present three-component photochemical protocol was demonstrated by the gram-scale reaction and product derivatization.