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Experimental Results and Mechanistic Insights on the Reactions of Indolylmethyl Acetates with Soft Carbon Pronucleophiles.
Arcadi, Antonio; Aschi, Massimiliano; Chiarini, Marco; Fabrizi, Giancarlo; Fochetti, Andrea; Goggiamani, Antonella; Iavarone, Federica; Iazzetti, Antonia; Serraiocco, Andrea; Zoppoli, Roberta.
Affiliation
  • Arcadi A; Dipartimento di Scienze Fisiche e Chimiche, Università degli Studi di L'Aquila; Via Vetoio, 67100 Coppito, AQ, Italy.
  • Aschi M; Dipartimento di Scienze Fisiche e Chimiche, Università degli Studi di L'Aquila; Via Vetoio, 67100 Coppito, AQ, Italy.
  • Chiarini M; Dipartimento di Bioscienze e Tecnologie Agro-alimentari e Ambientali, Università di Teramo, via R. Balzarini, 1, 64100 Teramo, TE, Italy.
  • Fabrizi G; Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy.
  • Fochetti A; Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy.
  • Goggiamani A; Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy.
  • Iavarone F; Dipartimento di Scienze Biotecnologiche di base, Cliniche Intensivologiche e Perioperatorie, Università Cattolica del Sacro Cuore, L.go Francesco Vito 1, 00168 Rome, Italy.
  • Iazzetti A; Policlinico Universitario 'A. Gemelli' Foundation-IRCCS, Rome 00168, Italy.
  • Serraiocco A; Dipartimento di Scienze Biotecnologiche di base, Cliniche Intensivologiche e Perioperatorie, Università Cattolica del Sacro Cuore, L.go Francesco Vito 1, 00168 Rome, Italy.
  • Zoppoli R; Policlinico Universitario 'A. Gemelli' Foundation-IRCCS, Rome 00168, Italy.
ACS Omega ; 9(26): 28450-28462, 2024 Jul 02.
Article in En | MEDLINE | ID: mdl-38973837
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 η3-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.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: ACS Omega Year: 2024 Document type: Article Affiliation country: Italy Country of publication: United States
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: ACS Omega Year: 2024 Document type: Article Affiliation country: Italy Country of publication: United States