An Efficient Stereoselective Synthesis of (E)-β-Fluoroalkenyliodonium Salts

Abstract

Stereoselective synthesis of (E)-β-fluoroalkenyliodonium salts was performed by the treatment of alk-1-ynes with p-iodo­toluene difluoride in the presence of HBF₄-Et₂O. The reaction occurred instantaneously at -78 °C to give the fluoroalkenyliodonium salts in good yields with high stereoselectivity. The Pd-catalyzed carbomethoxylation of the fluoroalkenyliodonium salt was also carried out to obtain a (E)-β-fluoro-α,β-unsaturated ester.

Key words

iodonium salt - fluoroalkene - p-iodotoluene difluoride - stereoselective synthesis - fluorination reaction

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