Stereodivergent Hydrohalogenation of SCF3 Alkynes and Cross-Coupling Reactions
Résumé
SCF3-substituted internal alkynes undergo regio-and stereoselective hydrohalogenation to provide the corresponding -halo--SCF3-alkenes. The regioselectivity is ensured by the strong polarization of the CC 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 -iodo--SCF3-alkenes was illustrated in several cross-coupling, protodeiodination, and cyanation reactions.