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Synthesis of Ortho/Ortho '-Substituted 1,1-Diarylethylenes through Cross-Coupling Reactions of Sterically Encumbered Hydrazones and Aryl Halides

  作者 ROCHE MAXIME; HAMZE ABDALLAH; PROVOT OLIVIER; BRION JEANDANIEL; ALAMI MOUAD  
  选自 期刊  Journal of Organic Chemistry;  卷期  2013年78-2;  页码  445-454  
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[摘要]The reactivity of sterically hindered N-tosylhydrazones 2 featuring ortho/ortho'-substituents on the aromatic ring with various ortho-, meta-, and para-substituted aryl halides 3 was investigated. To accomplish successfully this challenging coupling, fine-tuning of the reaction conditions were required. The newly established PdCl2(MeCN)(2)/Xphos/NaO-t-Bu/F-benzene system in a sealed tube is compatible with a broad spectrum of both coupling partners, regardless of their electronic and steric nature. This protocol has been applied successfully to the synthesis of a xanthene derivative.

 
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