To evaluate the feasibility of the proposal, we began exploring the reactivity of N-phenylsulfonyl allylanilines 1 as a model substrate class (Scheme 2A). However, only a moderate yield could be obtained with substrate 1a after extensive screening of conditions, due to the generation of undesired six-and five-membered heterocyclic products 2a' and 2a''. As shown in the mechanistic proposal, once the HAT from Co III -H species occurs, the generated radical can evolve towards three different products via ipso addition (2a) or ortho addition at the phenyl group attached to sulfur (2a') and nitrogen (2a''), respectively. To suppress this undesired, previously-reported radical ortho attack, we prepared two additional substrates with di-ortho and ortho substitution (1b and 1c, respectively).