Dam Dennis, Schoenmakers Joeri, Bouwman Elisabeth, Codée Jeroen D C
Leiden Institute of Chemistry, Universiteit Leiden, 2333 CC Leiden, The Netherlands.
J Org Chem. 2025 May 16;90(19):6577-6583. doi: 10.1021/acs.joc.5c00595. Epub 2025 May 3.
Aziridines are important structures in the contemporary organic synthesis and are used for several biological applications. Herein, we show that aziridines can be readily synthesized from alkenes by the reductive activation of sulfonyl azides, mediated by photoredox catalysis. Mechanistic studies indicate that the reaction proceeds through reactive nitrene radical anions instead of the more commonly encountered triplet nitrenes. A substrate scope is performed that showed good functional group compatibility.
氮丙啶是当代有机合成中的重要结构，并且用于多种生物学应用。在此，我们表明通过光氧化还原催化介导的磺酰叠氮的还原活化，可以很容易地从烯烃合成氮丙啶。机理研究表明，该反应通过活性氮烯自由基阴离子进行，而不是更常见的三线态氮烯。进行了底物范围研究，结果显示出良好的官能团兼容性。
