Intramolecular 1,5-C(Sp³)–H Radical Amination via Co(II)-Based Metalloradical Catalysis for Five-Membered Cyclic Sulfamides

Authors

Hongjian Lu, University of South Florida
Kai Lang, Boston College
Huiling Jiang, University of South Florida
Lukasz Wojtas, University of South FloridaFollow
X Peter Zhang, Boston College

Document Type

Article

Publication Date

7-28-2016

Digital Object Identifier (DOI)

https://doi.org/10.1039/C6SC02231F

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.

Rights Information

This work is licensed under a Creative Commons Attribution 3.0 License.

Was this content written or created while at USF?

Yes

Citation / Publisher Attribution

Chemical Science, v. 7, p. 6934-6939

Scholar Commons Citation

Lu, Hongjian; Lang, Kai; Jiang, Huiling; Wojtas, Lukasz; and Zhang, X Peter, "Intramolecular 1,5-C(Sp³)–H Radical Amination via Co(II)-Based Metalloradical Catalysis for Five-Membered Cyclic Sulfamides" (2016). Chemistry Faculty Publications. 30.
https://digitalcommons.usf.edu/chm_facpub/30