Visible-Light-Promoted Iron-Catalyzed Amidation/Cyclization of Arylacrylamides with Dioxazolones

A visible-light-promoted and simple iron salt-catalyzed cascade amidation/cyclization of <i>N</i>-aryl acrylamides with dioxazolones was developed. The reaction proceeds under photosensitizer-free conditions and features satisfactory to good yields, broad functional group tolerance, and an easy operation procedure. Mechanistic studies revealed that the reaction proceeded via an iron-nitrene intermediate. This method may contribute to shift the paradigm of iron-catalyzed C-N bond construction and nitrene transfer chemistry.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-12-17
DOI
https://doi.org/10.1021/acs.joc.5c02001
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Visible-Light-Promoted Iron-Catalyzed Amidation/Cyclization of Arylacrylamides with Dioxazolones

Shuxin Liang, Yan Du, Xiaoqiang Yu, Yi Wang
The Journal of Organic Chemistry
Radical Photochemical Reactions
article

Visible-Light-Promoted Iron-Catalyzed Amidation/Cyclization of Arylacrylamides with Dioxazolones

Shuxin Liang, Yan Du, Xiaoqiang Yu, Yi Wang
article en

Abstract

A visible-light-promoted and simple iron salt-catalyzed cascade amidation/cyclization of <i>N</i>-aryl acrylamides with dioxazolones was developed. The reaction proceeds under photosensitizer-free conditions and features satisfactory to good yields, broad functional group tolerance, and an easy operation procedure. Mechanistic studies revealed that the reaction proceeded via an iron-nitrene intermediate. This method may contribute to shift the paradigm of iron-catalyzed C-N bond construction and nitrene transfer chemistry.

The Journal of Organic ChemistryVol. 91(1)
Dalian University of Technology (CN), State Key Laboratory of Fine Chemicals
Openalex Percentile: Top 69%
Radical Photochemical Reactions
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Visible-Light-Promoted Iron-Catalyzed Amidation/Cyclization of Arylacrylamides with Dioxazolones — Shuxin Liang, Yan Du, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS