Efficient synthesis of dibenzo[a,c]cyclohepten-5-ones via a sequential Suzuki-Miyaura coupling and aldol condensation reaction

J Org Chem. 2009 May 15;74(10):3948-51. doi: 10.1021/jo900508z.

Abstract

A common strategy for the synthesis of a 7-membered-ring system with a Suzuki-Miyaura coupling followed by an acid/base-promoted intramolecular aldol condensation reaction has been developed. The reaction of 2'-bromoacetophenones with 2-formylphenylboronic acids in the presence of Pd(OAc)(2) and CataCXium PIntB L8 efficiently provided biaryl compounds, which were transformed to a wide array of dibenzo[a,c]cyclohepten-5-ones in excellent yields by a sequential treatment with p-TsOH, followed by 10% aq NaOH.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Cycloheptanes / chemical synthesis*
  • Cycloheptanes / chemistry
  • Ligands

Substances

  • Aldehydes
  • Cycloheptanes
  • Ligands
  • 3-hydroxybutanal