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Published on: May 21, 2019
Dual Functionalization of α-Aminoamides via Photocatalytic Intramolecular Oxygen Migration to Cyanomethylureas
Lili Duan1, Pinyong Zhong1, Huatao Shen1
1Jiangxi Provincial Key Laboratory of Functional Molecular Materials Chemistry, Jiangxi University of Science and Technology, Ganzhou 341000, China.
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.
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