Reaction development. We initiated the reaction development by screening experimental conditions for the coupling of N-chloro- It is speculated that many directing groups, along with the coupling partners, can trap transition metals in the non-reacting chelating states (e.g., III in Fig. ); only via competitive binding from directing group of the next catalytic cycle, the final turnover steps can occur. Structural elaboration of 2H-isoindole skeleton. The goal of SOS is to construct molecular skeletons without undesired appendages from the reactivity-assisting groups and exploit the reactivity of ring atoms for further structural elaboration (Fig. ). To this end, the ester groups on the C3 site of 2H-isoindoles should therefore be eliminated first. For proof-of-concept demonstration, 3wd was selected and subjected to deesterification reaction. The ester group can be removed to afford SOS target product 4 under Ni(OAc) 2 /dcype/Ph 3 SiH catalysis.