A mild and scalable one-pot synthesis of N-substituted 2-aminobenzimidazoles via visible light mediated cyclodesulfurization
Issued Date
2025-12-01
Resource Type
eISSN
20452322
Scopus ID
2-s2.0-85217832854
Pubmed ID
39900800
Journal Title
Scientific Reports
Volume
15
Issue
1
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SCOPUS
Bibliographic Citation
Scientific Reports Vol.15 No.1 (2025)
Suggested Citation
Rerkrachaneekorn T., Annuur R.M., Pornsuwan S., Sukwattanasinitt M., Wacharasindhu S. A mild and scalable one-pot synthesis of N-substituted 2-aminobenzimidazoles via visible light mediated cyclodesulfurization. Scientific Reports Vol.15 No.1 (2025). doi:10.1038/s41598-025-86772-8 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/105414
Title
A mild and scalable one-pot synthesis of N-substituted 2-aminobenzimidazoles via visible light mediated cyclodesulfurization
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Abstract
A visible light mediated photocatalyst-free synthesis of N-substituted 2-aminobenzimidazoles directly from o-phenylenediamines and isothiocyanates is developed in a one-pot fashion. This one-pot reaction proceeds through three steps: N-substitution of o-phenylenediamines, thiourea formation and visible light mediated cyclodesulfurization. This method enables the rapid and efficient synthesis of structurally diverse N-substituted 2-aminobenzimidazoles, achieving yields up to 92% across 69 examples. The practicality of the reaction is demonstrated by gram-scale synthesis. The key advantages of this method include the use of less toxic solvent in aqueous media, the elimination of photocatalyst, and a simple, practical setup (one-pot, open-flask, and ambient temperature). Mechanistic insights are gathered through control experiments, including light on/off cycles and radical inhibition studies. The results indicate that the reaction involves with radical pathway mediated by visible light.