Tan Eugene Yew Kun, Mat Lani Amirah S, Sow Wayne, Liu Yuliang, Li Haoyu, Chiba Shunsuke
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore, Singapore, 637371, Singapore.
Angew Chem Int Ed Engl. 2023 Oct 2;62(40):e202309764. doi: 10.1002/anie.202309764. Epub 2023 Aug 25.
The facile construction of C(sp )-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.
富含C(sp )的碳环和杂环化合物的简便构建是推动当代药物发现计划的关键合成策略。易于获得的二维(2D)平面芳烃的下游去芳构化是通向三维(3D)脂肪族支架的直接途径。在此，我们证明了多硫阴离子能够在可见光照射下，在甲酸钾和甲醇存在的情况下催化取代萘、吲哚和其他相关杂芳族化合物的去芳构化过程。所开发的方案具有广泛的官能团耐受性、操作简便、可扩展性和成本效益，是芳烃去芳构化的一种实用且可持续的合成工具。
