Cyano-aryl radical anions, analogous to I2, are readily generated and well precedented via SET using electrochemistry, being used both as a reagent or as an electron shuttle to reduce a reagent in situ -as in our mechanism. Chemical generation of this radical anionic intermediate is also precedented via base assisted homolytic aromatic substitution with deprotonation of an aryl radical via addition of a superstoichiometric base. Although this strategy has been limited to a highly restricted synthetic scope, with some methods also relying on toxic organomercury reagents. The aryl radical anion (I2) must then be oxidised to form the observed product, either (a) by a DABCO radical cation, thereby quenching the radical reaction (Fig. ); or (b) by reduction of another redox active ester, thereby propagating the reaction (Fig. ). This induces another fragmentation event directly, whilst avoiding the slower EDA complex fragmentation pathway.