Regio‐ and Stereoselective Hydroelementation of SF<sub>5</sub>‐Alkynes and Further Functionalizations.
Lucas Popek, Jorge Juan Cabrera‐Trujillo, Vincent Debrauwer, Nicolas Blanchard, Karinne Miqueu, Vincent Bizet
Abstract
Abstract Herein is described a fully regio‐ and stereoselective hydroelementation reaction of SF 5 ‐alkynes with N, O and S‐nucleophiles and further functionalization of the corresponding Z ‐(hetero)vinyl‐SF 5 intermediates, a suitable platform to access α‐SF 5 ketones and esters, β‐SF 5 amines and alcohols under mild reaction conditions. Experimental and computational comparative studies between SF 5 ‐ and CF 3 ‐alkynes have been performed to highlight and explain the difference of reactivity and selectivity observed between these two fluorinated motifs.
Topics & Concepts
StereoselectivityChemistryNucleophileSurface modificationSelectivityReactivity (psychology)RegioselectivityCombinatorial chemistryOrganic chemistryCatalysisAlternative medicineMedicinePhysical chemistryPathologyFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsCarbon dioxide utilization in catalysis