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.

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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

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article

Stereoselective synthesis of chalcogen-tethered γ-lactams via 5-exo-dig cyclisation under visible-light irradiation

Praveen Reddy Adiyala, Dharavath Ravi, Vadla Shiva Prasad, Vadithya Ranga Rao et al.
1 citations
Chemical Communications
Sulfur-Based Synthesis Techniques
0.94
article

Stereoselective synthesis of chalcogen-tethered γ-lactams via 5-exo-dig cyclisation under visible-light irradiation

Praveen Reddy Adiyala, Dharavath Ravi, Vadla Shiva Prasad, Vadithya Ranga Rao, Chelukalapally Anil Kumar, Silari MohanaKrishna
article en
1 citations

Abstract

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.

Chemical CommunicationsVol. 61(56)
Indian Institute of Chemical Technology (IN), Academy of Scientific and Innovative Research (IN)
Department of Science and Technology, Ministry of Science and Technology, India, Council of Scientific and Industrial Research, India, University Grants Commission
Openalex Percentile: Top 25%
Sulfur-Based Synthesis Techniques
0.94
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