Synthesis of 2,3-dihydro-1H-inden-1-one derivatives via Ni-catalyzed intramolecular hydroacylation

Fan Yang, Tienan Jin, Yoshinori Yamamoto

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

An efficient synthetic method for the formation of 2,3-dihydro-1H-inden-1- one derivatives through a Ni-catalyzed intramolecular hydroacylation of 2-(prop-2-ynyl)benzaldehydes has been developed. Examination of various nickel and other transition metal catalysts and phosphine ligands showed that the use of Ni(COD) 2 catalyst combined with P(i-Pr) 3 ligand was the best choice to the success of the present intramolecular hydroacylation. A wide range of functional groups were tolerated, affording the corresponding substituted α-lidene-2,3-dihydro-1H-inden-1-ones in good to high yields with a sole E-selectivity under present reaction conditions.

Original languageEnglish
Pages (from-to)5223-5228
Number of pages6
JournalTetrahedron
Volume68
Issue number26
DOIs
Publication statusPublished - 2012 Jul 1

Keywords

  • 2,3-Dihydro-1H-inden-1-ones
  • 2-(Prop-2-ynyl) benzaldehydes
  • Intramolecular hydroacylation
  • Nickel catalysts

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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