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Site-Selective Synthesis of Arylated Indenones by Suzuki-Miyaura Cross-Coupling Reactions of 2,3,5-Tribromoinden-1-one

  作者 ZINAD DHAFER SABER; HUSSAIN MUNAWAR; VILLINGER ALEXANDER; LANGER PETER  
  选自 期刊  European Journal of Organic Chemistry;  卷期  2011年-22;  页码  4212-4221  
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[摘要]The first transition-metal-catalyzed cross-coupling reactions of 2,3,5-tribromo-1H-inden-1-one are reported. The Suzuki-Miyaura reaction of 2,3,5-tribromo-1H-inden-1-one with three equivalents of arylboronic acid gave 2,3,5-triaryl-1H-inden-1-ones. The reaction with one and two equivalents of arylboronic acid gave 2,5-dibromo-3-aryl-1H-inden-1-ones and 5-bromo-2,3-diaryl-1H-inden-1-ones, respectively, with very good site-selectivity. The one-pot reaction of 2,3,5-tribromo-1H-inden-1-one with one equivalent of two different arylboronic acids afforded 5-bromo-2,3-diaryl-1H-inden-1-ones containing two different terminal aryl groups. Other one-pot reactions allowed the synthesis of 2,3,5-triaryl-1H-inden-1-ones containing different aryl groups.

 
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