Abstract
SCF3-substituted internal alkynes undergo regio- and stereoselective hydrohalogenation to provide the corresponding β-halo-α-SCF3-alkenes. The regioselectivity is ensured by the strong polarization of the C≡C triple bond in SCF3-alkynes, while the stereoselectivity is governed by the strength of the proton donor and/or by the solvent polarity. The potential of β-iodo-α-SCF3-alkenes was illustrated in several cross-coupling, protodeiodination, and cyanation reactions.
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