Synthesis of alkynylated selenophenes by site-selective sonogashira reactions of tetrabromoselenophene

Peter Ehlers, Tung T. Dang, Tamás Patonay, Alexander Villinger, Peter Langer

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7 Citations (Scopus)

Abstract

Mono-, di-, and tetraalkynylated selenophenes were prepared by site-selective Sonogashira reactions of tetrabromoselenophene. Aryl-, alkyl-, and trimethylsilylacetylenes were suitable substrates for this procedure. The first attack occurred regioselectively at C-2 and C-5. In addition, differently diarylated dialkynylselenophenes were prepared using site-selective Suzuki and Sonogashira reactions. Mono-, di-, and tetraalkynylated selenophenes can be ontained by site-selective Sonogashira reactions of tetrabromoselenophene. Aryl-, alkyl-, and trimethylsilylacetylenes are suitable starting materials. Differently diarylated dialkynylselenophenes can be synthesized by site-selective Suzuki and Sonogashira reactions.

Original languageEnglish
Pages (from-to)2000-2007
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number10
DOIs
Publication statusPublished - Apr 1 2013

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Keywords

  • Alkynes
  • Cross-coupling
  • Heterocycles
  • Palladium
  • Regioselectivity
  • Selenium

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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