2,3-Disubstituted 2,3,5-trisubstituted benzofurans by regioselective Pd-catalyzed cross-coupling reactions; a short synthesis of eupomatenoid-15

T. Bach, M. Bartels

Research output: Contribution to journalArticlepeer-review

32 Scopus citations

Abstract

2,3-Dibromobenzofuran (1) 2,3,5-tribromobenzofuran (2) undergo regioselective Sonogashira- Negishi-type cross-coupling reactions at the 2-position. Subsequent substitution reactions at C-3 are possible for the cross-coupling products obtained from compound 1. A regioselective functionalization of the 3,5-dibromobenzofurans derived from substrate 2 was achieved by an halogen-metal exchange which occurred selectively at the 3-position. In a conclusive reaction step cross-coupling reactions at C-5 were used to build up 2,3,5-trisubstituted benzofurans. As an example, the synthesis of eupomatenoid-15 (8) is described.

Original languageEnglish
Pages (from-to)1284-1286
Number of pages3
JournalSynlett
Issue number8
DOIs
StatePublished - 2001

Keywords

  • Catalysis
  • Cross-coupling
  • Heterocycles
  • Palladium
  • Regioselectivity

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