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

Year: 2025

Type: article

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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.5c01847

Authors: Lili Duan, Pinyong Zhong, Huatao Shen, Fumin Liao, Kunming Liu, Bin Huang, Nianhua Luo, Jin-Biao Liu

Institutions: Jiangxi University of Science and Technology, Gannan Medical University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: Education Department of Jiangxi Province

OpenAlex ID: W4416915372

FWCI: 0.293

Cites: 39

Cited by: 1

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