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

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

*Autore corrispondente per questo lavoro

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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