Issue 27, 2024

Simple, catalytic C(sp3)–H azidation using the C–H donor as the limiting reagent

Abstract

C–N bonds play a critical role in pharmaceutical, agrochemical, and materials sciences, necessitating ever-better methods to forge this linkage. Here we report a simple procedure for direct C(sp3)–H azidation using iron or manganese catalysis and a nucleophilic azide source. All reagents are commercially available, the experimental procedure is simple, and we can use the C–H donor substrate as the limiting reagent, a challenge for many C–H azidation methods. Preliminary experiments are consistent with a hydrogen atom transfer (HAT)/radical ligand transfer (RLT) radical cascade mechanism and a wide variety of substrates can be azidated in moderate to high yields.

Graphical abstract: Simple, catalytic C(sp3)–H azidation using the C–H donor as the limiting reagent

Supplementary files

Article information

Article type
Communication
Submitted
22 sept. 2023
Accepted
28 févr. 2024
First published
04 mars 2024

Chem. Commun., 2024,60, 3705-3708

Simple, catalytic C(sp3)–H azidation using the C–H donor as the limiting reagent

J. F. Hooson, H. N. Tran, K. Bian and J. G. West, Chem. Commun., 2024, 60, 3705 DOI: 10.1039/D3CC04728H

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