Iodonitrene-Mediated Nitrogen Transfer to Alkenes for the Direct Synthesis of NH-Aziridines
Yuri Gelato1, Laura Marraffa1, Francesco Pasca1
1Department of Pharmacy-Drug Sciences, University of Bari Aldo Moro, Via E. Orabona 4, Bari 70125, Italy.
Abstract:
This work presents a novel and efficient method for the direct synthesis of NH-aziridines from a broad range of alkenes under mild conditions. The developed method uses aqueous ammonia and (diacetoxyiodo)benzene (PIDA) at 0 °C, offering a straightforward and atom-economical approach. Notably, this approach addresses the common challenge of chemoselectivity, effectively preventing the overoxidation of aziridines to nitriles. Mechanistic studies support the involvement of an in situ-generated iodonitrene as the key nitrogen-transfer intermediate. Overall, this method represents a significant advancement in aziridine synthesis, combining simplicity and selectivity, and complements the existing procedures for the direct NH insertion into alkenes.
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