Stereodivergent\nHydrohalogenation of SCF<sub>3</sub> Alkynes and Cross- Coupling Reactions

SCF<sub>3</sub>-substituted internal alkynes undergo\nregio- and\nstereoselective hydrohalogenation to provide the corresponding β-halo-α-SCF<sub>3</sub>-alkenes. The regioselectivity is ensured by the strong polarization\nof the CC triple bond in SCF<sub>3</sub>-alkynes, while the\nstereoselectivity is governed by the strength of the proton donor\nand/or by the solvent polarity. The potential of β-iodo-α-SCF<sub>3</sub>-alkenes was illustrated in several cross-coupling, protodeiodination,\nand cyanation reactions.