Palladium-Catalyzed Acetoxylation of γ-Dehydro-aryl-himachalene: The Synthesis of a Novel Allylic Acetoxylated Sesquiterpene and a π-Allyl Palladium(II) Complex

Autor: Issam Louchachha, Abdelmajid Faris, Youssef Edder, Ali Hasnaoui, Anna Kozakiewicz-Piekarz, Abdelkarim Ait Mansour, Brahim Boualy, Rachid Salghi, Khalil Azzaoui, Rachid Sabbahi, Ashwag S. Alanazi, Mohamed Hefnawy, Belkheir Hammouti, Abdallah Karim, Mustapha Ait Ali
Jazyk: angličtina
Rok vydání: 2024
Předmět:
Zdroj: Molecules, Vol 29, Iss 21, p 5040 (2024)
Druh dokumentu: article
ISSN: 1420-3049
44650892
DOI: 10.3390/molecules29215040
Popis: Allylic oxygenated derivatives of himachalenes are highly valued molecules due to their potential applications in perfumery, cosmetics, and pharmaceuticals. Previous attempts at catalyzed allylic oxidation of himachalenes led to the formation of a very stable η3-allyl palladium complex, preventing any further reaction development. Herein, we present the first successful palladium-catalyzed synthesis of a novel allylic acetoxylated derivative of himachalenes. This reaction was achieved by incorporating an aromatic ring into the substrate structure. The resulting intermediate complex was isolated and characterized using nuclear magnetic resonance spectroscopy and X-ray crystallography. Density functional theory (DFT) calculations were performed to compare the reactivity of the newly synthesized complex with previously reported ones. The theoretical results confirm that the introduction of an aromatic ring enhances the reactivity of the η³-allyl palladium complex, thereby facilitating the desired transformation.
Databáze: Directory of Open Access Journals
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