Dearomatization of (Hetero)arenes through Photodriven Interplay between Polysulfide Anions and Formate**
Eugene Yew Kun Tan
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore, Singapore, 637371 Singapore
Search for more papers by this authorAmirah S. Mat Lani
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore, Singapore, 637371 Singapore
Search for more papers by this authorWayne Sow
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore, Singapore, 637371 Singapore
Search for more papers by this authorDr. Yuliang Liu
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore, Singapore, 637371 Singapore
Search for more papers by this authorDr. Haoyu Li
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore, Singapore, 637371 Singapore
Search for more papers by this authorCorresponding Author
Prof. Dr. Shunsuke Chiba
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore, Singapore, 637371 Singapore
Search for more papers by this authorEugene Yew Kun Tan
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore, Singapore, 637371 Singapore
Search for more papers by this authorAmirah S. Mat Lani
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore, Singapore, 637371 Singapore
Search for more papers by this authorWayne Sow
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore, Singapore, 637371 Singapore
Search for more papers by this authorDr. Yuliang Liu
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore, Singapore, 637371 Singapore
Search for more papers by this authorDr. Haoyu Li
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore, Singapore, 637371 Singapore
Search for more papers by this authorCorresponding Author
Prof. Dr. Shunsuke Chiba
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore, Singapore, 637371 Singapore
Search for more papers by this authorA previous version of this manuscript has been deposited on a preprint server (https://doi.org/10.26434/chemrxiv-2023-kccqn).
Abstract
The facile construction of C(sp3)-rich carbo- and heterocyclic compounds is a pivotal synthetic strategy to foster contemporary drug discovery programs. The downstream dearomatization of readily accessible two-dimensional (2D) planar arenes represents a direct pathway towards accessing three-dimensional (3D) aliphatic scaffolds. Here, we demonstrate that polysulfide anions are capable of catalyzing a dearomatization process of substituted naphthalenes, indoles, and other related heteroaromatic compounds in the presence of potassium formate and methanol under visible light irradiation. The developed protocol exhibits broad functional group tolerance, operational simplicity, scalability, and cost-effectiveness, representing a practical and sustainable synthetic tool for the arene dearomatization.
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.
Supporting Information
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| Filename | Description |
|---|---|
| ange202309764-sup-0001-23.cif608 KB | Supporting Information |
| ange202309764-sup-0001-24_Me.cif794.4 KB | Supporting Information |
| ange202309764-sup-0001-28.cif972.1 KB | Supporting Information |
| ange202309764-sup-0001-37.cif304.6 KB | Supporting Information |
| ange202309764-sup-0001-41.cif372.6 KB | Supporting Information |
| ange202309764-sup-0001-42.cif200.4 KB | Supporting Information |
| ange202309764-sup-0001-45.cif333.4 KB | Supporting Information |
| ange202309764-sup-0001-47.cif465.7 KB | Supporting Information |
| ange202309764-sup-0001-48.cif467.9 KB | Supporting Information |
| ange202309764-sup-0001-56.cif621.2 KB | Supporting Information |
| ange202309764-sup-0001-59.cif766.5 KB | Supporting Information |
| ange202309764-sup-0001-72.cif514.2 KB | Supporting Information |
| ange202309764-sup-0001-79.cif713.3 KB | Supporting Information |
| ange202309764-sup-0001-misc_information.pdf27.9 MB | Supporting Information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
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