STEREOSPECIFIC ALKENYLATION OF C-H BONDS VIA REACTION WITH BETA-HETEROATOM-FUNCTIONALIZED TRISUBSTITUTED VINYL TRIFLONES

Aryl and alkyl beta-heteroatom-trisubstituted vinyl triflones react wi th THF and cyclohexane to undergo trifluoromethyl radical-mediated C-H functionalization reactions to afford E and Z beta-heteroatom-trisubs tituted olefins. Most reactions proceed with both high yield and high stereospecificity (retention of configuration). beta-Substituents whic h have been employed in this study are iodine, bromine, fluorine, benz oate, ethylcarbonate, and phthalimide. beta-Substituents bearing power ful electron-releasing groups such as alkoxy or amino render the vinyl triflone unreactive.