Direct Regioselective Hydro(hetero)arylation/Cyclocondensation Reactions of β-(2-Aminophenyl)-α,β-ynones by Means of Transition-Metal Catalysis/Brønsted Acid Synergism: Experimental Results and Computational Insights

Vincenzo Marsicano, Antonio Arcadi*, Massimiliano Aschi, Marco Chiarini, Giancarlo Fabrizi, Antonella Goggiamani, Fabio Marinelli, Antonia Iazzetti

*Corresponding author

Research output: Contribution to journalArticle

Abstract

Experimental results and computational insights explain the key role of transition-metal catalysis/Bronsted acid synergism in the achievement of the sequential regioselective direct heteroarylation/ cyclocondensation reactions of beta-(2-aminophenyl)-alpha,beta-ynones with a variety of electron-rich aromatic heterocyclic/arenes to afford quinoline-(hetero)aromatic hybrids. The first approach to the synthesis of 4-(1H-pyrrol-2-yl)quinolines is described. The effectiveness of various transition metals is compared.
Original languageEnglish
Pages (from-to)6857-6867
Number of pages11
JournalJournal of Organic Chemistry
Volume88
DOIs
Publication statusPublished - 2023

Keywords

  • Catalysis
  • Cyclocondensation Reactions
  • Transition-metal catalysis

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