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2018-05-25

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/128153

Palladium catalysis in intramolecular carbene C-H insertion of α-diazo-α-(methoxycarbonyl)acetamides to form β-lactams

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https://doi.org/10.1002/ejoc.201800666

Abstract

The intramolecular carbene C-H insertion of α‐diazo‐α‐(methoxycarbonyl)acetamides leading to β‐lactams is effectively catalyzed by palladium complexes. It is found that although Pd0 catalysts typically produce mixtures of β‐lactams together with Buchner‐type reaction products, the use of PdII catalysts results in highly chemoselective transformations. According to DFT calculations, this insertion reaction occurs stepwise and involves an unprecedented PdII‐promoted Mannich‐type reaction through a metallacarbene‐induced zwitterionic intermediate.

Subject

Pal·ladi (Element químic), Catàlisi, Síntesi orgànica, Complexitat computacional

Subject (English)

Palladium, Catalysis, Organic synthesis, Computational complexity

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

Citation

SOLÉ ARJÓ, Daniel, et al. Palladium catalysis in intramolecular carbene C-H insertion of α-diazo-α-(methoxycarbonyl)acetamides to form β-lactams. European Journal of Organic Chemistry. 2018. Vol. 2018, num. 32, pags. 4446-4455. ISSN 1434-193X. [consulted: 11 of August of 2026]. Available at: https://hdl.handle.net/2445/128153

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