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.
Authors
- Jin‐Biao Liu (ORCID: https://orcid.org/0000-0002-5038-6541)
- Hao Shen (ORCID: https://orcid.org/0000-0001-8875-6491)
- Pinyong Zhong (ORCID: https://orcid.org/0000-0003-0825-8586)
- Kunming Liu (ORCID: https://orcid.org/0000-0003-4654-4081)
- Nianhua Luo (ORCID: https://orcid.org/0000-0002-0233-849X)
- Fumin Liao (ORCID: https://orcid.org/0000-0001-8679-737X)
- Bin Huang (ORCID: https://orcid.org/0000-0002-5407-6209)
- Lili Duan
Institutions
- Institute of Molecular Functional Materials (CN)
- Gannan Medical University (CN)
- Jiangxi University of Science and Technology (CN)
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
- 0.00