Modular Synthesis of Furans with Four Nonidentical Substituents by Aqueous Defluorinative Reaction of Trifluoromethyl Enones with Two Nucleophiles
Xueying Huang, Shu‐Ji Gao, Danhua Ge, Mengtao Ma, Zhi‐Liang Shen, Xue‐Qiang Chu
Abstract
A three-component reaction of trifluoromethyl enones, phosphine oxides, and alcohols in water solution is developed. This defluorinative reaction occurs through a cascade process involving defluorophosphorylation, defluoroalkyloxylation, and defluoroheteroannulation, enabling the modular synthesis of furans with four distinct substituents: C 2-alkyloxy, C 3-trifluoromethyl, C 4-phosphoryl, and C 5-(hetero)aryl groups. Moreover, apart from alcohol substrates, the scope of nucleophiles could be further extended to phenols, azacycles, or sulfonamide.
Topics & Concepts
ChemistryNucleophileTrifluoromethylArylPhosphinePhenolsAlcoholOrganic chemistrySulfonamideAqueous solutionCombinatorial chemistryMedicinal chemistryCatalysisAlkylFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions