Experimental Results and Mechanistic Insights on the Reactions of Indolylmethyl Acetates with Soft Carbon Pronucleophiles

Antonio Arcadi, Massimiliano Aschi, Marco Chiarini, Giancarlo Fabrizi*, Andrea Fochetti, Antonella Goggiamani, Federica Iavarone, Antonia Iazzetti*, Andrea Serraiocco, Roberta Zoppoli

*Autore corrispondente per questo lavoro

Risultato della ricerca: Contributo in rivistaArticolo in rivista

Abstract

The palladium-catalyzed reaction of N-protected 2-indolylmethyl acetates with soft carbon pronucleophiles is described. Besides the formation of the expected coupling reaction at the C1 ' position, unprecedented attack at the C3 position of the plausible eta(3)-indolyl-palladium intermediate has been observed, and the selectivity control C1 '/C3 seems to depend on the nature of the protecting group and ligand. The reactivity of 3-indolylmethyl acetates has also been also investigated. Quantum chemical calculations support the experimental results.
Lingua originaleEnglish
pagine (da-a)1-13
Numero di pagine13
RivistaACS Omega
DOI
Stato di pubblicazionePubblicato - 2024

Keywords

  • indole-2-carbinol
  • 2- indolylmethyl acetates
  • palladium
  • indole-3-carbinol

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