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

Year: 2024

Type: article

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.

Source: Advanced Synthesis & Catalysis

DOI: 10.1002/adsc.202401183

Authors: Debora Schiroli, Aleksandr Voronov, Francesco Pancrazzi, Nunzio Iraci, Salvatore Vincenzo Giofrè, Beatrice Macchi, Valeria Stefanizzi, Raffaella Mancuso, Bartolo Gabriele, Paolo Pio Mazzeo, Luca Capaldo, Nicola Della Ca'

Institutions: University of Parma, University of Messina, University of Rome Tor Vergata, University of Calabria, Consorzio Interuniversitario Reattività Chimica e Catalisi

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,430

OpenAlex ID: W4404016887

FWCI: 0.989

Cites: 48

Cited by: 7

Related to: 10