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Intramolecular 1,5-C(sp3)-H Radical Amination via Co(II)-Based Metalloradical Catalysis for Five-Membered Cyclic
Hongjian Lu1, Kai Lang2, Huiling Jiang3
1Department of Chemistry, University of South Florida, Tampa, FL 33620, USA.; The Institute of Chemistry & Biomedical Sciences, Nanjing University, Nanjing, 210093, P. R. China.
Abstract:
Co(II)-based metalloradical catalysis (MRC) proves effective for intramolecular 1,5-C-H amination of sulfamoyl azides under neutral and nonoxidative conditions, providing a straightforward approach to access strained 5-membered cyclic sulfamides with nitrogen gas as the only byproduct. The metalloradical amination system is applicable to different types of C(sp3)-H bonds and has a high degree of functional group tolerance. Additional features of the Co(II)-catalyzed 1,5-C-H amination include excellent chemoselectivity toward allylic and propargylic C-H bonds. The unique reactivity and selectivity profile of the Co(II)-catalyzed 1,5-C-H amination is attributed to the underlying radical mechanism of MRC.
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