Bulletin of the Chemical Society of Japan p. 1542 - 1553 (1991)
Update date:2022-07-29
Topics:
Miura, Katsukiyo
Takeyama, Yoshihiro
Oshima, Koichiro
Utimoto, Kiitiro
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.
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