Science of Synthesis

Ibrahim, H., Science of Synthesis: C-1 Building Blocks in Organic Synthesis, (2014) 2, 205.

Conceptually related to the carbonylation of aziridines, the carbonylation of 3-monosubstituted diaziridines ‌50‌ to yield 1,3-diazetidin-2-ones ‌51‌ (aza-β-lactams) is catalyzed by 5 mol% of bis(dibenzylideneacetone)palladium(0) in dimethylformamide at 120 °C under atmospheric pressure of carbon monoxide (‌Scheme 16‌).[‌24‌] Carbon monoxide insertion occurs regiospecifically into the N—N bond. Interestingly, the reaction does not proceed with 3,3-disubstituted diaziridines, but these substrates can be carbonylated with stoichiometric amounts of octacarbonyldicobalt(0).[‌24‌]

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References