Heck-oxyarylation of 2-phenyl-2H-chromenes and 1,2-dihydronaphthalenes

Katalin Gulácsi, István Németh, Ádám Szappanos, Kinga Csillag, Tünde Zita Illyés, Tibor Kurtán, Sándor Antus

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Abstract

The Heck-oxyarylation of racemic 2-phenyl-2H-chromene [(±)-4b] and 1 2-dihydronaphthalenes (14a,b) has been studied with 2-chloromercuriphenols (5a-d) in the presence of Li2[PdCl4] catalyst The reactions resulted in the diastereoselective formation of racemic 6-phenylpterocarpans of (6R 6aR, 11aR) relative configuration [(±)-8a-d] and their dibenzo[1 3]dioxocine analogues [(±)-12a-d] as main products respectively The ratio of products and the lack of regioisomeric products (13a-d) corroborated the cationic mechanism of the oxyarylation of 2H-chromenes which has been also supported by the transformation of 14a,b under similar conditions.

Original languageEnglish
Pages (from-to)137-141
Number of pages5
JournalCroatica Chemica Acta
Volume86
Issue number2
DOIs
Publication statusPublished - Jul 1 2013

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Keywords

  • Catalysis
  • Dibenzo[d,g][1,3]dioxocines
  • Oxidative coupling
  • Palladium(0)
  • Pterocarpans
  • Reaction mechanism

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Gulácsi, K., Németh, I., Szappanos, Á., Csillag, K., Illyés, T. Z., Kurtán, T., & Antus, S. (2013). Heck-oxyarylation of 2-phenyl-2H-chromenes and 1,2-dihydronaphthalenes. Croatica Chemica Acta, 86(2), 137-141. https://doi.org/10.5562/cca2103