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Synthesis and Molecular Structure of Symmetrical 1,8-Diarylnaphthalenes

  作者 PIETERS GREGORY; TERRASSON VINCENT; GAUCHER ANNE; PRIM DAMIEN; MARROT JEROME  
  选自 期刊  European Journal of Organic Chemistry;  卷期  2010年-30;  页码  5800-5806  
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[摘要]The synthesis of substituted 1,8-diarylnaphthalenes is reported. A bis-Suzuki coupling strategy starting from 1,8-di-bromonaphthalene provides a useful and general route to the 1,8-diarylnaphthalene scaffold. In this context, N-heterocyclic benzhydrylamine ligands, in combination with PdCl2, were found to form especially efficient catalytic systems. The syn/anti ratios were determined in solution from their H-1 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 pi-stacking between cofacial rings.

 
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