An unusual, mild and convenient one-pot two-step access to (E)-stilbenes from hydroxy-substituted benzaldehydes and phenylacetic acids under microwave activation: a new facet of the classical Perkin reaction

Arun K. Sinha, Vinod Kumar, Abhishek Sharma, Anuj Sharma, Rakesh Kumar

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71 Scopus citations

Abstract

A mild and convenient one-pot two-step synthesis of hydroxystilbenes with trans selectivity has been developed through a modified Perkin reaction between benzaldehydes and phenylacetic acids bearing 4- or 2-hydroxy substitution at the aromatic ring, in the presence of piperidine-methylimidazole and polyethylene glycol under microwave irradiation. The observation of a simultaneous condensation-decarboxylation leading to the unusual formation of hydroxystilbenes in lieu of α-phenylcinnamic acid reveals an interesting facet to the classical Perkin reaction. The developed protocol provides a green alternative to the prevalent methods employing a toxic decarboxylating agent in the form of quinoline/Cu salt, and the requirement for harsh protection-deprotection steps for the synthesis of hydroxylated stilbenes.

Original languageEnglish
Pages (from-to)11070-11077
Number of pages8
JournalTetrahedron
Volume63
Issue number45
DOIs
StatePublished - 5 Oct 2007

Keywords

  • (E)-Stilbenes
  • C-C coupling
  • Decarboxylation
  • Microwave
  • Perkin reaction

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