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Issue 12, 2016
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Intramolecular 1,5-C(sp3)–H radical amination via Co(ii)-based metalloradical catalysis for five-membered cyclic sulfamides

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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.

Graphical abstract: Intramolecular 1,5-C(sp3)–H radical amination via Co(ii)-based metalloradical catalysis for five-membered cyclic sulfamides

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Supplementary files

Article information


Submitted
20 May 2016
Accepted
25 Jul 2016
First published
28 Jul 2016

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2016,7, 6934-6939
Article type
Edge Article
Author version available

Intramolecular 1,5-C(sp3)–H radical amination via Co(II)-based metalloradical catalysis for five-membered cyclic sulfamides

H. Lu, K. Lang, H. Jiang, L. Wojtas and X. P. Zhang, Chem. Sci., 2016, 7, 6934
DOI: 10.1039/C6SC02231F

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