Electrochemical fluoro-selenenylation of electron-deficient olefins

Electrochemical fluoro-selenenylation of electron-deficient olefins like a,p-unsaturated ester, carboxylic acid, amide, and phosphonate was successfully carried out by the anodic oxidation of diphenyl diselenide in the presence of olefins in Et3N center dot 5HF/CH3NO2. The anodically generated benzeneselenenyl fluoride [PhSeF] equivalent was stable in the electrolytic solution, which resulted in the efficient fluoro-selenenylation. The fluoro-selenenylation products were shown to be potential useful fluoro-building blocks. (C) 2008 Elsevier Ltd. All rights reserved.