Xiong Biquan, Xu Shipan, Liu Yu, Tang Ke-Wen, Wong Wai-Yeung
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, P. R. China.
Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Hong Kong, P. R. China.
J Org Chem. 2021 Jan 15;86(2):1516-1527. doi: 10.1021/acs.joc.0c02390. Epub 2021 Jan 7.
A simple and efficient method for the regioselective thiolation of -quinone methides with sodium aryl/alkyl sulfinates has been established using an acid/phosphine-induced radical route under transition-metal-free conditions. A broad range of sodium aryl/alkyl sulfinates and -quinone methides (-QMs) are compatible for the reaction, giving the expected products with good to excellent yields. Control experiments were also performed to gain insights into the generation mechanism of thiyl radicals and hydrogen-atom transfer process. This protocol provides a safe and feasible way for the formation of carbon-sulfur bonds.
在无过渡金属条件下，利用酸/膦诱导的自由基途径，建立了一种简单有效的方法，用于用芳基/烷基亚磺酸钠对醌甲基化物进行区域选择性硫醇化反应。多种芳基/烷基亚磺酸钠和醌甲基化物（-QMs）都能与该反应兼容，以良好至优异的产率得到预期产物。还进行了对照实验，以深入了解硫自由基的生成机制和氢原子转移过程。该方法为碳-硫键的形成提供了一种安全可行的途径。
