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Palladium - dppb - borate-catalyzed regioselective synthesis of cinnamate esters by alkoxycarbonylation of phenylacetylene

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25 Scopus citations

Abstract

The regiosetective alkoxycarbonylation of phenylacetylene into various cinnamate esters was achieved with a catalyst system formed from palladium (II), 1,4-bis(diphenylphosphino) butane (dppb) and salicylborate complex in acetonitrile as a solvent. The influence of various parameters on the overall conversion of phenylacetylene and the selectivity of the reaction were studied systematically by varying the type of palladium complex, acids promoter, CO pressure, temperature and the reaction time. This investigation allowed us to obtain the predominant formation of cinnamate esters with excellent selectivity (90-96%).

Original languageEnglish
Pages (from-to)553-559
Number of pages7
JournalApplied Organometallic Chemistry
Volume22
Issue number10
DOIs
StatePublished - Oct 2008

Keywords

  • Alkoxycarbonylation
  • Boric acid
  • Cinnamate esters
  • Palladium
  • Phenylacetylene
  • Phosphine
  • Salicylic acid
  • Unsaturated esters

ASJC Scopus subject areas

  • General Chemistry
  • Inorganic Chemistry

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