Evidence for the interaction between tBuOK and 1,10-phenanthroline to form the 1,10-phenanthroline radical anion: a key step for the activation of aryl bromides by electron transfer

Abstract

Electron paramagnetic resonance and electrochemistry are used to evidence the interaction between 1,10-phenanthroline (Phen) and KO^tBu to form the 1,10-phenanthroline radical anion, Phen˙⁻, and the ^tBuO˙ radical via an inner-sphere electron transfer. In addition, electrochemistry is also used to explain the formation of aryl radicals from aryl bromides via outer-sphere electron transfer from the key intermediate Phen˙⁻.