Chen Huafeng, Zhai Lei, Zuo Yulan, Qin Xi, Zhang Jinling, Tian Kui, Xu Peng
Department of Chemistry and Chemical Engineering, Chongqing University of Science and Technology, Chongqing, 401331, P.R. China.
Precis Chem. 2023 Oct 23;1(10):602-607. doi: 10.1021/prechem.3c00093. eCollection 2023 Dec 25.
We herein report a simultaneous dehalogenation and hydrogenation (DHH) reaction in Sonogashira coupling involving hexahalogenobenzene CX (X = I, Br), in which a halogen on the aryl polyhalide substrate was substituted by a hydrogen atom. First, a steric bulky terminal alkyne was designed and synthesized to study the influence of the reaction conditions (e.g., catalyst, solvent, temperature) and the halogens on the substrates CX on the DHH reaction. Moreover, based on the optimized conditions, a terminal alkyne with less steric hindrance was further synthesized to investigate the influence of alkyne on the DHH reaction. As a result, two aromatic polyynes and were obtained in the DHH process, and their photophysical properties were further studied and compared. The influence produced by the alkynes and aryl polyhalides substrate provide insights into Sonogashira coupling involving terminal alkyne with huge steric hindrance and polyhalogenated aromatic hydrocarbons.
我们在此报告了在涉及六卤代苯CX（X = I，Br）的Sonogashira偶联反应中的同时脱卤和氢化（DHH）反应，其中芳基多卤化物底物上的一个卤素被氢原子取代。首先，设计并合成了一种空间位阻较大的末端炔烃，以研究反应条件（例如催化剂、溶剂、温度）以及底物CX上的卤素对DHH反应的影响。此外，基于优化的条件，进一步合成了一种空间位阻较小的末端炔烃，以研究炔烃对DHH反应的影响。结果，在DHH过程中获得了两种芳族多炔烃 和 ，并对它们的光物理性质进行了进一步研究和比较。炔烃和芳基多卤化物底物所产生的影响为涉及具有巨大空间位阻的末端炔烃和多卤代芳烃的Sonogashira偶联反应提供了见解。
