Taking inspiration from the approaches described above -and work from the Shenvi group on a hydroarylative Truce-Smiles rearrangement employing a stoichiometric manganese reagent for HAT (Scheme 1d) -we sought to develop a catalytic MHAT platform for hydroarylation. We rationalised that use of the reductive MHAT catalytic system, that our group and others have developed in the last years, may enable the formation of -arylethylamines via the following sequence: polarity-matched HAT from a Co III -H species (formed by reduction and protonation of a Co II catalyst); followed by radical aryl migration and reduction and protonation of the resulting Ncentered radical to form the product. However, we were aware that obtaining the desired products from ipso substitution could prove challenging due to the competitive, previously reported orthocyclisation pathway (Scheme 1e). Herein, we report our studies in the development of a photoinduced hydroarylation strategy of N-arylsulfonyl allylanilines, demonstrating how substrate design can yield desired products with highly sterically substituted arene rings.