A straightforward total synthesis of a small panel of natural benzo[c]phenanthridines is described. The selective coupling of an aryl triflate with a bromobenzylamine by means of palladium/norbornene joint catalysis and a sequential transfer hydrogenation deliver these alkaloids in one pot. Dihydrophenanthridines initially formed undergo dehydrogenation smoothly while norbornene acts both as a catalyst for their assembly and as a sacrificial olefin in their dehydrogenation. Palladium catalysis is a powerful tool for organic chemistry and found wide applications in synthesis owing to its versatility. By employing readily available substrates many protocols for the selective formation of C–C and C–Heteroatom bonds were reported in the last two decades. A powerful strategy in the construction of cyclic scaffolds is based on the use of reagents possessing a suitably tethered (masked) nucleophile which could terminate the catalytic cycle by reacting with an electrophilic organopalladium(II) intermediate. In this context, the association of a palladium salt with norbornene delivers a remarkable catalytic system that allows the multiple functionalization of an aryl halide in one pot. After seminal work by Catellani, many synthetic applications were reported which delivers complex polycyclic scaffolds adopting this strategy. In the context of nitrogen heterocycles, methods that deliver carbazoles, phenanthridines or dibenzoazepines have been reported and this variety clearly demonstrates the large scope of this catalytic system. An efficient synthesis of phenanthridines from aryl iodides and bromobenzylamines is accessible by merging a palladium/norbornene co-catalyzed formation 1 In honor of Professor Victor Sniekus on 77th Birthday HETEROCYCLES, Vol. 88, No. 1, 2014 807