Stereoselective synthesis of chalcogen-tethered <i>γ</i>-lactams <i>via</i> 5-<i>exo-dig</i> cyclisation under visible-light irradiation
We report a rapid, eco-friendly, and catalyst-free method for the stereoselective synthesis of chalcogen-tethered γ-lactams under visible-light irradiation. Using dimethyl carbonate as a green solvent, the reaction proceeds <i>via</i> 5-<i>exo-dig</i> intramolecular radical cyclization, affording <i>Z</i>-configured γ-lactams with high selectivity and broad substrate scope, including sulfur and selenium derivatives. The protocol is operationally simple, metal-free, and aligns with green chemistry principles. Notably, its translation to continuous-flow conditions using a K<sub>3</sub>PO<sub>4</sub> glass-packed reactor significantly improved the reaction rate and yield, demonstrating excellent scalability. This approach offers a sustainable and efficient route to valuable chalcogenated γ-lactams, relevant to medicinal and synthetic chemistry.
Authors
- Praveen Reddy Adiyala
- Dharavath Ravi (ORCID: https://orcid.org/0000-0003-1983-0357)
- Vadla Shiva Prasad
- Vadithya Ranga Rao
- Chelukalapally Anil Kumar
- Silari MohanaKrishna
Institutions
- Indian Institute of Chemical Technology (IN)
- Academy of Scientific and Innovative Research (IN)
Publication Details
- Journal
- Chemical Communications
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5cc01525a
- Citations
- 1
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- Department of Science and Technology, Ministry of Science and Technology, India
- Council of Scientific and Industrial Research, India
- University Grants Commission