Dual Functionalization of α-Aminoamides via Photocatalytic Intramolecular Oxygen Migration to Cyanomethylureas

A green and efficient visible-light-driven strategy for direct cyanomethylurea synthesis from α-aminoamides and isothiocyanates via intramolecular oxygen migration is reported. This method merges cyanation and ureidation in a single step, leveraging the amide oxygen as a dual synthon to forge nitrile (C≡N) and urea (C═O) bonds. Operating under metal-free, ambient conditions (room temperature, air, visible light), the protocol accommodates diverse substrates without toxic reagents. Mechanistic studies implicate light-mediated desulfurization and oxygen atom transfer, offering a sustainable strategy for one-step dual functionalization of bioactive molecules.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-12-02
DOI
https://doi.org/10.1021/acs.joc.5c01847
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

Dual Functionalization of α-Aminoamides via Photocatalytic Intramolecular Oxygen Migration to Cyanomethylureas

Jin‐Biao Liu, Hao Shen, Pinyong Zhong, Kunming Liu et al.
The Journal of Organic Chemistry
Radical Photochemical Reactions
article

Dual Functionalization of α-Aminoamides via Photocatalytic Intramolecular Oxygen Migration to Cyanomethylureas

Jin‐Biao Liu, Hao Shen, Pinyong Zhong, Kunming Liu, Nianhua Luo, Fumin Liao, Bin Huang, Lili Duan
article en

Abstract

A green and efficient visible-light-driven strategy for direct cyanomethylurea synthesis from α-aminoamides and isothiocyanates via intramolecular oxygen migration is reported. This method merges cyanation and ureidation in a single step, leveraging the amide oxygen as a dual synthon to forge nitrile (C≡N) and urea (C═O) bonds. Operating under metal-free, ambient conditions (room temperature, air, visible light), the protocol accommodates diverse substrates without toxic reagents. Mechanistic studies implicate light-mediated desulfurization and oxygen atom transfer, offering a sustainable strategy for one-step dual functionalization of bioactive molecules.

The Journal of Organic ChemistryVol. 90(49)
Institute of Molecular Functional Materials (CN), Gannan Medical University (CN), Jiangxi University of Science and Technology (CN)
Openalex Percentile: Top 71%
Radical Photochemical Reactions
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