A mild and scalable one-pot synthesis of N-substituted 2-aminobenzimidazoles via visible light mediated cyclodesulfurization
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...
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| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Nature Portfolio
2025-02-01
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| Series: | Scientific Reports |
| Subjects: | |
| Online Access: | https://doi.org/10.1038/s41598-025-86772-8 |
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| Summary: | 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. |
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| ISSN: | 2045-2322 |