Three-Component Coupling of Acyl Fluorides, Silyl Enol Ethers, and Alkynes by P(III)/P(V) Catalysis
Hayato Fujimoto, Momoka Kusano, Takuya Kodama, Mamoru Tobisu
Abstract
We report herein on the phosphine-catalyzed hydrovinylation reaction by three-component coupling of acyl fluorides, silyl enol ethers, and alkynoates. The key to the success of the reaction is the formal transmetalation between pentacoordinate P(V) species (i.e., fluorophosphorane) and a silyl enol ether, which allows for C-C bond formation between the polarity-mismatched sites. The bond formation that cannot be attained even by transition metal catalysis is accomplished by a P(III)/P(V) manifold.
Topics & Concepts
ChemistrySilyl enol etherEnolSilylationSilyl etherCatalysisPhosphineTransmetalationMedicinal chemistryEnol etherEtherCoupling reactionOrganic chemistryStereochemistryFluorine in Organic ChemistryOrganoboron and organosilicon chemistryCatalytic Cross-Coupling Reactions