Issue 10, 2015

The development of carbene-stabilized N–O radical coupling strategy in metal-free regioselective C–H azidation of quinoline N-oxides

Abstract

Although radical oxidative coupling provides a powerful C–H functionalization tool, the selective coupling of an electrophilic radical with a heterocyclic electron-deficient C2 site is still a seemingly impossible challenge. In this work, an efficient oxidative C2–H azidation of quinoline N-oxides with TMSN3 has been developed, proceeding at room temperature within 10 min. Based on control experiments and detailed EPR studies, the reaction appears to involve a novel carbene-stabilized N–O radical intermediate, which undergoes a single electron transfer to TMSN3 to give the C2-azidation product. Moreover, this procedure could be smoothly scaled up to gram-synthesis and the products could be converted into other functional heterocycles.

Graphical abstract: The development of carbene-stabilized N–O radical coupling strategy in metal-free regioselective C–H azidation of quinoline N-oxides

Supplementary files

Article information

Article type
Research Article
Submitted
26 Jun 2015
Accepted
19 Jul 2015
First published
20 Jul 2015

Org. Chem. Front., 2015,2, 1313-1317

The development of carbene-stabilized N–O radical coupling strategy in metal-free regioselective C–H azidation of quinoline N-oxides

P. Li, J. Zhao, C. Xia and F. Li, Org. Chem. Front., 2015, 2, 1313 DOI: 10.1039/C5QO00204D

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