Synthesis of 2-(1,4-dioxaspiro[4.5]decan-6-yl)acrylamides from 2-acetylcyclohexanone via palladium-catalysed aminocarbonylation

Roland Farkas, Andea Petz, László Kollár

Research output: Contribution to journalArticle

Abstract

6-(1-Iodovinyl)-1,4-dioxaspiro[4.5]decane, an iodoalkene obtained from 2-acetylcyclohexanone via ethylene ketal formation, hydrazone formation and iodination, was aminocarbonylated in the presence of a palladium-phosphine precatalyst. Systematic investigations revealed that 2-(1,4-dioxaspiro[4.5]decan-6-yl)acrylamides can be obtained in high yields via palladium-catalysed aminocarbonylation. The influence of the amine nucleophiles and of the reaction conditions on the isolated yields was investigated. Graphical abstract: (Chemical Equation Presented).

Original languageEnglish
Pages (from-to)1665-1671
Number of pages7
JournalMonatshefte fur Chemie
Volume146
Issue number10
DOIs
Publication statusPublished - Oct 7 2015

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Keywords

  • Amine nucleophile
  • Carbon monoxide
  • Carbonylation
  • Iodoalkene
  • Palladium catalyst

ASJC Scopus subject areas

  • Chemistry(all)

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