Premium
Synthesis and Molecular Structure of Symmetrical 1,8‐Diarylnaphthalenes
Author(s) -
Pieters Grégory,
Terrasson Vincent,
Gaucher Anne,
Prim Damien,
Marrot Jerôme
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000685
Subject(s) - chemistry , planarity testing , steric effects , context (archaeology) , stereochemistry , stacking , naphthalene , catalysis , suzuki reaction , combinatorial chemistry , crystallography , organic chemistry , paleontology , palladium , biology
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.