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Triplet nitrene-mediated photocatalytic azidation of tertiary C(sp³)–H bonds

01 October 2025, Version 1
Working Paper
This content is an early or alternative research output and has not been peer-reviewed by Cambridge University Press at the time of posting.

Abstract

A photocatalytic C(sp³)–H azidation involving a triplet nitrene as a hydrogen atom abstractor is described. The key nitrene intermediate is generated through energy transfer to a sulfonyl azide, which also functions as an azide source. This method exhibits excellent selectivity for tertiary C–H bonds and is applicable to leucine-containing dipeptides.

Keywords

energy transfer
nitrene
C–H functionalization
azide

Supplementary materials

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Description
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Experimental details, computational study, characterization data, and NMR spectra
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Version History

Oct 01, 2025 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2025-87kmx
D O I: 10.26434/chemrxiv-2025-87kmx [opens in a new tab]

Funding

Japan Society for the Promotion of Science
JP22K15248
Japan Society for the Promotion of Science
JP25K09894
Japan Agency for Medical Research and Development
JP22ama121034
Japan Agency for Medical Research and Development
JP22ama121042
Japan Science and Technology Agency
JPMJSP2110

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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