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Synfacts 2024; 20(04): 0367
DOI: 10.1055/s-0043-1773173
Metals in Synthesis

Palladium-Catalyzed Carbonylative Cycloaddition of Acylsilanes and Imines to Access β-Lactams

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Phillip Pommerening
Inagaki T, Kodama T, Tobisu M. * Osaka University, Suita, Japan
Catalytic Synthesis of β-Lactam Derivatives by Carbonylative Cycloaddition of Acylsilanes with Imines via a Palladium Fischer-Carbene Intermediate.

Nat. Catal. 2024;
7: 132-138
DOI: 10.1038/s41929-023-01081-5.
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Key words

acylsilanes - cycloaddition - Fischer carbenes - imines - β-lactams - palladium catalysis

Significance

Tobisu and co-workers disclosed a palladium-catalyzed protocol for the carbonylative cycloaddition of acylsilanes and imines to form highly functionalized β-lactams. The key feature of this reaction is the generation of a Fischer-type ­palladium siloxycarbene complex from the acylsilane, as verified by X-ray crystallographic analysis.


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Comment

The carbon monoxide gas required for the formation of the ketene intermediate is formed in situ by decarbonylation of the acylsilane. The shown mechanism is supported by density functional theory calculations and experimental investigations, which exclude a photo-induced isomerization of the acylsilane to a siloxycarbene.


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Publication History

Article published online:
13 March 2024

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