Synthesis of Indole/Benzofuran-Containing Diarylmethanes through Palladium-Catalyzed Reaction of Indolylmethyl or Benzofuranylmethyl Acetates with Boronic Acids

Antonia Iazzetti, Antonio Arcadi, Andrea Calcaterra, Marco Chiarini, Giancarlo Fabrizi, Andrea Fochetti, Antonella Goggiamani, Federico Marrone, Vincenzo Marsicano, Andrea Serraiocco

Risultato della ricerca: Contributo in rivistaArticolo in rivista

Abstract

The palladium-catalyzed synthesis of indole/benzofurancontaining diarylmethanes starting from indolylmethyl or benzofuranylmethyl acetates with boronic acids has been investigated. The success of the reaction is influenced by the choice of precatalyst: with indolylmethyl acetates the reaction works well with [Pd(η3-C3H5)Cl]2/XPhos while with benzofuranylmethyl acetates Pd2(dba)3/XPhos is more efficient. The good to high yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2- and 3-substituted indoles and 2-benzo[b]furans. The methodology can be advantageously extended to the preparation of a key precursor of Zafirlukast.
Lingua originaleEnglish
pagine (da-a)741-753
Numero di pagine13
RivistaSynthesis
Volume54
DOI
Stato di pubblicazionePubblicato - 2021

Keywords

  • Suzuki-Miyaura reaction
  • benzofurans
  • boronic acids
  • diarylmethanes
  • indoles
  • palladium

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