Nickel(0)/NaHMDS adduct-mediated intramolecular alkylation of unactivated arenes via a homolytic aromatic substitution mechanism

A variety of polycycles can be synthesized via an intramolecular alkylation cyclization promoted by Ni(PPh3)(4) and NaHMDS. Mechanistic investigations support the catalytic nature of Ni-0 in the course of TEMPO scavenging experiments and its association with the substrate and NaHMDS to form an adduct by DOSY NMR.