Triethylborane Induced Perfluoroalkylation of Silyl Enol Ethers and Ketene Silyl Acetals with Perfluoroalkyl Iodides

Article abstract of DOI:10.1246/bcsj.64.1542

Reaction of perfluoroalkyl iodides with silyl enol ethers mediated by Et3B in the presence of base such as 2,6-dimethylpyridine provides mixtures of perfluoroalkylated trialkylsilyl enol ethers and α-perfluoroalkylated ketones.The yield and distribution of the products heavily depend on the nature of base employed.Treatment of a reaction mixture consisting of perfluoroalkylated silyl enol ether and α-perfluoroalkylated ketone with concd HCl in THF gives α-perfluoroalkylated ketone as a single product.Reaction of ketene silyl acetals with perfluoroalkyl iodides in the absence of base affords α-perfluoroalkylated esters in excellent yields.