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

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Carbonylation
Derivatives
Hydrazones
Nucleophiles
Palladium
Substrates
Isomers
Amines
Esters
ethylene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of 2-naphthylacrylamides and 2-naphthylacrylates via homogeneous catalytic carbonylation of 1-iodo-1-naphthylethene derivatives. / Takács, Attila; Farkas, Roland; Petz, Andrea; Kollár, László.

In: Tetrahedron, Vol. 65, No. 25, 20.06.2009, p. 4795-4800.

Research output: Contribution to journalArticle

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