To achieve the synthesis of belts, we examined initially Ni(0)-promoted multiple intramolecular homocoupling reactions between neighboring bromoaryl moieties of 4c as a model transformation (Table ). After screening various reaction parameters, we were delighted to find out that when a combination of Ni(cod)2 (16 equiv.) and 2,2'-bipyridine (2,2'-bpy) (16 equiv.) was used as transition metal mediator in boiling tetrahydrofuran (THF), addition of a solution of substrate 4c through a syringe pump within 1 h and continuous heating of the resulting mixture for another 12 h led to the production of Pleasingly, belt [7]pyrrole [7]pyridine 5b was synthesized similarly in 23% yield from macrocycle 4b. Since eight and seven carbon-carbon bonds were formed during a one-pot reaction process, a chemical yield of 21% and 23% for 5c and 5b, respectively, implied a yield of higher than 80% in each carbon-carbon bond forming step. Under the identical reaction conditions, however, belt [6]pyrrole [6]pyridine 5a was isolated in 5% yield from 4a. The difficulty to construct a smaller belt homolog was most probably due to the substantial ramp-up of the macrocyclic strain during the belt-forming process (vide infra).