Combining Hydrodefluorination and Defluorophosphorylation for Chemo- and Stereoselective Synthesis of <i>gem</i>-Fluorophosphine Alkenes
Ya‐Fei Hu, Man-Hang Feng, Peng‐Yuan Zhang, Hao Xu, Mengtao Ma, Zhi‐Liang Shen, Xue‐Qiang Chu
Abstract
A chemo-, regio-, and stereoselective reaction of trifluoromethyl enones, phenylsilane, and phosphine oxides through a sequential hydrodefluorination and defluorophosphorylation relay is developed for the synthesis of distinctive gem -fluorophosphine alkenes. This multicomponent reaction occurred under transition-metal-free conditions with good functional group tolerance. Moreover, the preinstalled carbonyl auxiliary is important for tuning the reactivity of β-trifluoromethyl enones, thereby enabling controllable and selective functionalization of two fluorine atoms in trifluoromethylated enones.
Topics & Concepts
ChemistryStereoselectivityTrifluoromethylPhenylsilaneFluorinePhosphineReactivity (psychology)Combinatorial chemistryOrganic chemistryMedicinal chemistryCatalysisPathologyAlternative medicineMedicineAlkylFluorine in Organic ChemistryChemical Synthesis and AnalysisCarbohydrate Chemistry and Synthesis