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2019-09-30

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cc-by (c) Solé Arjó, Daniel et al., 2019
Si us plau utilitzeu sempre aquest identificador per citar o enllaçar aquest document: https://hdl.handle.net/2445/151045

Site selectivity in Pd-catalyzed reactions of α-diazo-α-(methoxycarbonyl)acetamides: effects of catalysts and substrate substitution in the synthesis of oxindoles and ß-lactams

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Recurs relacionat

https://doi.org/10.3390/molecules24193551

Resum

The Pd-catalyzed intramolecular carbene C-H insertion of α-diazo-α-(methoxycarbonyl)acetamides to prepare oxindoles as well as β-lactams was studied. In order to identify what factors influence the selectivity of the processes, we explored how the reactions are affected by the catalyst type, using two oxidation states of Pd and a variety of ligands. It was found that, in the synthesis of oxindoles, ((IMes)Pd(NQ))2 can be used as an alternative to Pd2(dba)3 to catalyze the carbene CArsp2-H insertion, although it was less versatile. On the other hand, it was demonstrated that the Csp3-H insertion leading to β-lactams can be effectively promoted by both Pd(0) and Pd(II) catalysts, the latter being most efficient. Insight into the reaction mechanisms involved in these transformations was provided by DFT calculations.

Matèries

Teoria del funcional de densitat, Diazocomposts, Pal·ladi (Element químic)

Matèries (anglès)

Density functionals, Diazo compounds, Palladium

Citació

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Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)

Citació

SOLÉ ARJÓ, Daniel, et al. Site selectivity in Pd-catalyzed reactions of α-diazo-α-(methoxycarbonyl)acetamides: effects of catalysts and substrate substitution in the synthesis of oxindoles and ß-lactams. Molecules. 2019. Vol. 24, num. 19, pags. 3551. ISSN 1420-3049. [consulted: 4 of August of 2026]. Available at: https://hdl.handle.net/2445/151045

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