Synthesis of 2-naphthylacrylamides and 2-naphthylacrylates via homogeneous catalytic carbonylation of 1-iodo-1-naphthylethene derivatives

Attila Takács, Roland Farkas, Andrea Petz, László Kollár

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Two highly reactive iodoalkenes (1-iodo-1-(2-naphthyl)ethene and 1-iodo-1-(1-naphthyl)ethene) were prepared from the corresponding acetonaphthone isomers via their hydrazones and used as substrates in palladium-catalysed carbonylations. Both iodoalkenyl substrates proved to be highly reactive in the presence of various N-nucleophiles and the corresponding N-substituted naphthylacrylamides were formed chemoselectively in nearly quantitative yields. High isolated yields (up to 93%) were achieved with all types of amines under mild reaction conditions. The alkoxycarbonylation of the above iodoalkenes resulted in esters of unexpectedly good isolated yields (up to 77%).

Original languageEnglish
Pages (from-to)4795-4800
Number of pages6
JournalTetrahedron
Volume65
Issue number25
DOIs
Publication statusPublished - Jun 20 2009

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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