Issue 61, 2023

Visible light-mediated ring-ablative functionalization of oxazoles: oxidative azidation and demethylative amination

Abstract

Photochemical functionalization of alkoxyoxazoles with trimethylsilyl azide and N,N-dimethylanilines is described. These C–N bond forming reactions proceed with concomitant oxidative ring-opening assisted by organic dyes as photocatalyst and molecular oxygen, providing access to novel chemical space. Unusual demethylative C–N bond formation in the case of N,N-dimethylanilines establishes a new reactivity pattern for these precursors.

Graphical abstract: Visible light-mediated ring-ablative functionalization of oxazoles: oxidative azidation and demethylative amination

Supplementary files

Article information

Article type
Communication
Submitted
16 Apr 2023
Accepted
03 Jul 2023
First published
04 Jul 2023

Chem. Commun., 2023,59, 9360-9363

Visible light-mediated ring-ablative functionalization of oxazoles: oxidative azidation and demethylative amination

P. Garg, T. Singh and A. Singh, Chem. Commun., 2023, 59, 9360 DOI: 10.1039/D3CC01871G

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