Abstract Teraryl-based α-helix mimetics have proven to be useful compounds for the inhibition of protein–protein interactions (PPI). We have developed a modular and flexible approach for the synthesis of teraryl-based α-helix mimetics. Central to our strategy is the use of a benzene core unit featuring two leaving groups of differentiated reactivity in the Pd- catalyzed cross-coupling used for terphenyl assembly. With the halogen/diazonium route ...