Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, P. R. China.
Laboratory and Research Base Management, Nanjing Agricultural University, Nanjing 210095, P. R. China.
J Org Chem. 2023 Feb 17;88(4):2069-2078. doi: 10.1021/acs.joc.2c02377. Epub 2023 Jan 26.
An electro-triggered cascade cyclization strategy was disclosed with concomitant phosphinylation and -heterocycle construction. It provides a novel and environmentally friendly approach to access phosphinyl-substituted -heterocycles with no external metal catalyst, oxidant, or heating. Mechanistic studies have revealed that anodic oxidation of H-phosphorus compounds occurs first to generate the key P-centered radical directly and cathodic reduction leads to the concurrent release of molecular hydrogen or methane. This protocol features simple operation, broad substrate scope, clean and mild conditions, and atom and step economy to form heterocycle-containing organophosphorus scaffolds.
一种电触发级联环化策略被揭示，同时实现膦酰化和杂环构建。它提供了一种新颖的、环保的方法，无需外部金属催化剂、氧化剂或加热，即可获得膦基取代的杂环化合物。机理研究表明，H-磷化合物的阳极氧化首先发生，直接生成关键的 P 中心自由基，而阴极还原导致分子氢或甲烷的同时释放。该方案具有操作简单、底物范围广、条件清洁温和、原子经济性和步骤经济性等特点，可形成含杂环的有机磷支架。
