Nagar Bhawana, Dhar Basab Bijayi
Department of Chemistry, School of Natural Sciences, Shiv Nadar University, Dadri, Gautam Buddha Nagar, UP 201314, India.
J Org Chem. 2022 Mar 4;87(5):3195-3201. doi: 10.1021/acs.joc.1c02924. Epub 2022 Feb 11.
In the presence of eosin Y, a visible light-induced one-step procedure (isolated yield of ≥75%) for thiolation of substituted 1,4-naphthoquinones using various aromatic and aliphatic thiols at room temperature is described herein. The rate-determining step of the reaction is thiyl radical generation, and the radical was characterized by high-resolution mass spectrometry. Cost effectiveness, operational simplicity, a short reaction time, high atom economy, and a very good yield make this photoredox-mediated process a useful alternative to the transition metal (e.g., Cu, Ag, and Pd)-catalyzed coupling reaction of quinones with thiols or disulfides.
本文描述了在曙红Y存在下，在室温下使用各种芳香族和脂肪族硫醇对取代的1,4-萘醌进行硫醇化的可见光诱导一步法（分离产率≥75%）。该反应的速率决定步骤是硫自由基的产生，并且通过高分辨率质谱对该自由基进行了表征。成本效益、操作简便、反应时间短、原子经济性高以及产率良好，使得这种光氧化还原介导的过程成为醌与硫醇或二硫化物的过渡金属（例如Cu、Ag和Pd）催化偶联反应的一种有用替代方法。
