Electrochemical iodofluorination of electron-deficient olefins
摘要:
Electron-deficient olefins like alpha,beta-unsaturated ester, amide, and phosphonate reacted with iodonium cation species generated by the anodic oxidation of iodide anion in Et3N-5HF/CH3NO2 to form corresponding iodofluorinated compounds in good to moderate yields. The reaction proceeds at room temperature under air atmosphere and constant current conditions. The iodofluorinated products were shown to be useful fluorine-containing building blocks. (C) 2009 Elsevier Ltd. All rights reserved.
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.