Palladium-catalyzed Tsuji-Trost-type reaction of benzofuran-2-ylmethyl acetates with nucleophiles

Antonia Iazzetti, Antonio Arcadi, Giancarlo Fabrizi, Andrea Fochetti, Francesca Ghirga, Antonella Goggiamani, Federico Marrone, Giulia Mazzoccanti, Andrea Serraiocco

Risultato della ricerca: Contributo in rivistaArticolo in rivista

Abstract

The palladium-catalyzed benzylic-like nucleophilic substitution of benzofuran-2-ylmethyl acetate with N, S, O and C soft nucleophiles has been investigated. The success of the reaction is dramatically influenced by the choice of catalytic system: with nitrogen based nucleophiles the reaction works well with Pd2(dba)3/dppf, while with sulfur, oxygen and carbo-nucleophiles [Pd(η3-C3H5)Cl]2/XPhos is more efficient. The regiochemical outcome shows that the nucleophilic substitution occurs only on the benzylic position of the η3-(benzofuryl)methyl complex. The high to excellent yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2-substituted benzo[b]furans. This journal is
Lingua originaleEnglish
pagine (da-a)909-917
Numero di pagine9
RivistaRSC Advances
Volume11
DOI
Stato di pubblicazionePubblicato - 2020

Keywords

  • Palladium catalysis, Tsuji–Trost-type reaction
  • benzofurans

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