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Article Dans Une Revue European Journal of Organic Chemistry Année : 2010

Synthesis and Molecular Structure of Symmetrical 1,8‐Diarylnaphthalenes

Résumé

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.

Domaines

Chimie

Dates et versions

hal-04429622 , version 1 (31-01-2024)

Identifiants

Citer

Grégory Pieters, Vincent Terrasson, Anne Gaucher, Damien Prim, Jerôme Marrot. Synthesis and Molecular Structure of Symmetrical 1,8‐Diarylnaphthalenes. European Journal of Organic Chemistry, 2010, 2010 (30), pp.5800-5806. ⟨10.1002/ejoc.201000685⟩. ⟨hal-04429622⟩
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