/sci/ - Science & Math

This probably is stupid as all fuck to chemists, but I'm a dumb babby still at the starting stages.

https://pubs.rsc.org/en/content/articlelanding/2016/ob/c5ob02034d

This is a reaction to hydrogenate a double bond while aminating one side and "ketonating"/"dioxidating" the other one, using pretty much just water and the aminating agent NBS. The mechanism seems pretty straightforward. Seeing as conditions are quite neutral and mild, it's just a matter of the water's oxygen, a nucleophile, attacking the most electrophilic side of the bromonium ion [4]. A benzylic carbon is much more electrophilic than a terminal carbon, so it receives the oxygen while the bromine settles on the other side.

My question is, to invert the regioselectivity, would it be simply a matter of making sure the benzylic carbon less electrophilic than the other side of the double bond? Would it work if the substrate's benzene ring had a strong EDG substituent or if the terminal carbon had a strong EWG substituent? For that matter, if that EWG were a hydroxyl, could this reaction turn it into an aldehyde?