Functionalization of the 3-position of thiophene and benzo[b]thiophene moieties by palladium-catalyzed C-C bond forming reactions using diazonium salts

Mõnica Raduán, Joaquim Padrosa, Anna Pla-Quintana, Teodor Parella, Anna Roglans

Research output: Contribution to journalArticleResearchpeer-review

24 Citations (Scopus)

Abstract

The palladium-catalyzed Matsuda-Heck and Suzuki-Miyaura cross-couplings of 2-methoxycarbonylthiophene-3-diazonium tetrafluoroborate 1 were performed to synthesize a series of thiophene derivatives functionalized in the β-position. Good to excellent yields of the cross-coupling products were obtained using palladium acetate [Pd(OAc)2], a ligandless palladium catalyst, without a base, at room temperature, under aerobic conditions and with short reaction times. A diazotization and cross-coupling sequence can also be performed in a one-pot process avoiding the isolation of the thiophenediazonium salt derivative. In addition, 2-methoxycarbonylbenzo[b]thiophene-3-diazonium tetrafluoroborate 8 was also efficiently arylated by applying the same Suzuki-Miyaura optimized reaction conditions. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Original languageEnglish
Pages (from-to)2003-2012
JournalAdvanced Synthesis and Catalysis
Volume353
Issue number11-12
DOIs
Publication statusPublished - 1 Aug 2011

Keywords

  • benzo[b]thiophenes
  • diazonium salts
  • Matsuda-Heck reactions
  • palladium
  • Suzuki-Miyaura cross-couplings
  • thiophenes

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