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

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公開日
2011-06
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/ejoc.201100313
公開者
Wiley

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<jats:title>Abstract</jats:title><jats:p>The first transition‐metal‐catalyzed cross‐coupling reactions of 2,3,5‐tribromo‐1<jats:italic>H</jats:italic>‐inden‐1‐one are reported. The Suzuki–Miyaura reaction of 2,3,5‐tribromo‐1<jats:italic>H</jats:italic>‐inden‐1‐one with three equivalents of arylboronic acid gave 2,3,5‐triaryl‐1<jats:italic>H</jats:italic>‐inden‐1‐ones. The reaction with one and two equivalents of arylboronic acid gave 2,5‐dibromo‐3‐aryl‐1<jats:italic>H</jats:italic>‐inden‐1‐ones and 5‐bromo‐2,3‐diaryl‐1<jats:italic>H</jats:italic>‐inden‐1‐ones, respectively, with very good site‐selectivity. The one‐pot reaction of 2,3,5‐tribromo‐1<jats:italic>H</jats:italic>‐inden‐1‐one with one equivalent of two different arylboronic acids afforded 5‐bromo‐2,3‐diaryl‐1<jats:italic>H</jats:italic>‐inden‐1‐ones containing two different terminal aryl groups. Other one‐pot reactions allowed the synthesis of 2,3,5‐triaryl‐1<jats:italic>H</jats:italic>‐inden‐1‐ones containing different aryl groups.</jats:p>

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