α-Fluoroalkylation of carbonyl compounds mediated by a highly reactive alkyl-rhodium complex

Treatment of silyl enol ethers of various carbonyl compounds with Et2Zn and fluoroalkyl halides (Rf–X) in the presence of RhCl(PPh3)3 in DME gave the corresponding α-Rf carbonyl compounds. A highly reactive alkyl-rhodium complex which was derived from RhCl(PPh3)3 and Et2Zn must be crucial in this reaction by accelerating the reaction rate and improving the yields dramatically. This reaction overcomes difficulties on the synthesis of α-Rf carbonyl compounds due to inverse polarization of Rf–X.

Graphical abstractThe treatment of silyl enol ethers with fluoroalkyl halides (Rf–X) and Et2Zn in the presence of RhCl(PPh3)3 gave α-fluoroalkylated ketones.Figure optionsDownload full-size imageDownload as PowerPoint slide