Synthesis and Molecular Structure of Symmetrical 1,8‐Diarylnaphthalenes

Abstract The synthesis of substituted 1,8‐diarylnaphthalenes is reported. A bis‐Suzuki coupling strategy starting from 1,8‐dibromonaphthalene provides a useful and general route to the 1,8‐diarylnaphthalene scaffold. In this context, N‐heterocyclic benzhydrylamine ligands, in combination with PdCl 2 , were found to form especially efficient catalytic systems. The syn / anti ratios were determined in solution from their 1 H NMR spectra. Analysis of the molecular structure in the solid state for six new targets focused on deformation of the naphthalene core. The observed lack of planarity occurs as a result of several parameters, such as the nature and number of substituents, the substitution pattern as well as steric congestion and π‐stacking between cofacial rings.