Additive carbonylations typically necessitate strong nucleophiles, such as alcohols or amines. Inthis study, we carbonylated a poorly nucleophilic urea, under oxidant-free conditions. Our straightforwardcarbonylative strategy enables access to versatile α,β-unsaturated γ-lactams featuring an aminocarbonylfragment, utilizing readily available propargylic ureas as starting materials. The employment of the PdI2/KIcatalytic system allowed complete regioselectivity (5-endo-dig), high functional group tolerance, broadsubstrate scope as well as operational simplicity (oxidant-free, organic ligand-free and base-free protocol). Thesynthetic utility of these γ-lactams is showcased through late-stage functionalizations, such as Giese reactionsand peptide couplings

Direct Access to α,β-Unsaturated γ-Lactams via Palladium-Catalysed Carbonylation of Propargylic Ureas / Schiroli, D.; Voronov, A.; Pancrazzi, F.; Iraci, N.; Vincenzo Giofrè, S.; Macchi, B.; Stefanizzi, V.; Mancuso, R.; Gabriele, B.; Mazzeo, P. P.; Capaldo, L.; Della Ca', N.. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - (2024). [10.1002/adsc.202401183]

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

Schiroli D.;Voronov A.;Pancrazzi F.;Mazzeo P. P.;Capaldo L.;Della Ca' N.
2024-01-01

Abstract

Additive carbonylations typically necessitate strong nucleophiles, such as alcohols or amines. Inthis study, we carbonylated a poorly nucleophilic urea, under oxidant-free conditions. Our straightforwardcarbonylative strategy enables access to versatile α,β-unsaturated γ-lactams featuring an aminocarbonylfragment, utilizing readily available propargylic ureas as starting materials. The employment of the PdI2/KIcatalytic system allowed complete regioselectivity (5-endo-dig), high functional group tolerance, broadsubstrate scope as well as operational simplicity (oxidant-free, organic ligand-free and base-free protocol). Thesynthetic utility of these γ-lactams is showcased through late-stage functionalizations, such as Giese reactionsand peptide couplings
2024
Direct Access to α,β-Unsaturated γ-Lactams via Palladium-Catalysed Carbonylation of Propargylic Ureas / Schiroli, D.; Voronov, A.; Pancrazzi, F.; Iraci, N.; Vincenzo Giofrè, S.; Macchi, B.; Stefanizzi, V.; Mancuso, R.; Gabriele, B.; Mazzeo, P. P.; Capaldo, L.; Della Ca', N.. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - (2024). [10.1002/adsc.202401183]
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/3009934
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 0
  • ???jsp.display-item.citation.isi??? ND
social impact