Synthesis of indenols and indanones via catalytic cyclic vinylpalladation of aromatic aldehydes

Vladimir Gevorgyan, Long Guo Quan, Yoshinori Yamamoto

Research output: Contribution to journalArticle

133 Scopus citations

Abstract

o-Bromobenzaldehyde 1, in the presence of a palladium catalyst, smoothly underwent consecutive intermolecular carbopalladation with internal alkynes 2 and then intramolecular nucleophilic vinylpalladation of the aldehyde function to produce the indenol derivatives 4 in high yields. Further heating of 4 under more elevated temperature caused complete isomerization to the corresponding indanones 8. A mechanism for this nucleophilic vinylpalladation of aromatic aldehydes is proposed.

Original languageEnglish (US)
Pages (from-to)4089-4092
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number21
DOIs
StatePublished - May 21 1999
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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