Direct Access to α,β‐Unsaturated γ‐Lactams via Palladium‐Catalysed Carbonylation of Propargylic Ureas.

Abstract Additive carbonylations typically necessitate strong nucleophiles, such as alcohols or amines. In this study, we carbonylated a poorly nucleophilic urea, under oxidant‐free conditions. Our straightforward carbonylative strategy enables access to versatile α,β‐unsaturated γ‐lactams featuring an aminocarbonyl fragment, utilizing readily available propargylic ureas as starting materials. The employment of the PdI 2 /KI catalytic system allowed complete regioselectivity ( 5‐endo‐dig ), high functional group tolerance, broad substrate scope as well as operational simplicity (oxidant‐free, organic ligand‐free and base‐free protocol). The synthetic utility of these γ‐lactams is showcased through late‐stage functionalizations, such as Giese reactions and peptide couplings.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2024-11-03
DOI
https://doi.org/10.1002/adsc.202401183
Citations
2
Primary Topic
Asymmetric Hydrogenation and Catalysis
Type
article
Field-Weighted Citation Impact
0.32
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article

Direct Access to α,β‐Unsaturated γ‐Lactams via Palladium‐Catalysed Carbonylation of Propargylic Ureas.

Beatrice Macchi, Valeria Stefanizzi, Aleksandr Voronov, Nicola Della Ca’ et al.
2 citations
Advanced Synthesis & Catalysis
Asymmetric Hydrogenation and Catalysis
0.32
article

Direct Access to α,β‐Unsaturated γ‐Lactams via Palladium‐Catalysed Carbonylation of Propargylic Ureas.

Beatrice Macchi, Valeria Stefanizzi, Aleksandr Voronov, Nicola Della Ca’, Bartolo Gabriele, Raffaella Mancuso, Luca Capaldo, Francesco Pancrazzi, Nunzio Iraci, Paolo P. Mazzeo, Salvatore V. Giofrè, Debora Schiroli
article en
2 citations

Abstract

Abstract Additive carbonylations typically necessitate strong nucleophiles, such as alcohols or amines. In this study, we carbonylated a poorly nucleophilic urea, under oxidant‐free conditions. Our straightforward carbonylative strategy enables access to versatile α,β‐unsaturated γ‐lactams featuring an aminocarbonyl fragment, utilizing readily available propargylic ureas as starting materials. The employment of the PdI 2 /KI catalytic system allowed complete regioselectivity ( 5‐endo‐dig ), high functional group tolerance, broad substrate scope as well as operational simplicity (oxidant‐free, organic ligand‐free and base‐free protocol). The synthetic utility of these γ‐lactams is showcased through late‐stage functionalizations, such as Giese reactions and peptide couplings.

Advanced Synthesis & CatalysisVol. 367(5)
University of Messina (IT), University of Rome Tor Vergata (IT), University of Parma (IT), Consorzio Interuniversitario Reattività Chimica e Catalisi (IT), University of Calabria (IT)
Openalex Percentile: Top 48%
Asymmetric Hydrogenation and Catalysis
0.32
DOIOpen Access PDFOpenAlex
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