Palladium-catalyzed sabinene oxidation with hydrogen peroxide : smart fragrance production and DFT insights.

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MetadadosDescriçãoIdioma
Autor(es): dc.creatorVieira, Camila Grossi-
Autor(es): dc.creatorAngnes, Ricardo Almir-
Autor(es): dc.creatorBraga, Ataualpa Albert Carmo-
Autor(es): dc.creatorGusevskaya, Elena Vitalievna-
Autor(es): dc.creatorRossi, Liane Marcia-
Data de aceite: dc.date.accessioned2025-08-21T15:53:16Z-
Data de disponibilização: dc.date.available2025-08-21T15:53:16Z-
Data de envio: dc.date.issued2023-05-17-
Data de envio: dc.date.issued2023-05-17-
Data de envio: dc.date.issued2021-
Fonte completa do material: dc.identifierhttp://www.repositorio.ufop.br/jspui/handle/123456789/16589-
Fonte completa do material: dc.identifierhttps://www.sciencedirect.com/science/article/pii/S2468823121006490-
Fonte completa do material: dc.identifierhttps://doi.org/10.1016/j.mcat.2021.112033-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/capes/1026597-
Descrição: dc.descriptionFragrance substances derived from natural sources are essential to the fine chemical industry, being an interesting task to pursue. Herein, we present a smart catalytic oxidation route for bio-renewable (1R,5R)-sabinene obtainment in acetonitrile or acetone, just using Pd(OAc)2 as catalyst and hydrogen peroxide as an final oxidant. The products obtained from (1R,5R)-sabinene and their mixtures have a distinct and pleasant smell and therefore are candidates for fragrance and pharmacological applications. Three oxyfunctionalized products were obtained with ca. 80% combined selectivity at high substrate conversions. The major products, two novel isomeric carane-type ketones with a bicyclo[4.1.0] skeleton, were formed by expanding the five-membered ring in the sabinene molecule, while (-)-sabina ketone was produced as a minor product. An uncommon mechanistic route was suggested and supported by density functions theory (DFT), which could suitably explain the formation of these ketones. DFT results supported a proposed concerted mechanism for the Csingle bondC activation, like a semipinacol rearrangement, which includes a heterolysis of the Pd-C bond and synchronous cleavage of the Csingle bondC bond in an intermediate organopalladium peroxo complex. We highly believe that such findings allow a step forward a deep understanding of such organic transformation, helping in future new routes for value-added products.-
Formato: dc.formatapplication/pdf-
Idioma: dc.languageen-
Direitos: dc.rightsrestrito-
Palavras-chave: dc.subjectDensity functions theory study-
Título: dc.titlePalladium-catalyzed sabinene oxidation with hydrogen peroxide : smart fragrance production and DFT insights.-
Aparece nas coleções:Repositório Institucional - UFOP

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