Zhang Lizhu, Wei Cunbo, Wu Jiawen, Liu Dan, Yao Yinchao, Chen Zhuo, Liu Jianxun, Yao Chang-Jiang, Li Dinghua, Yang Rongjie, Xia Zhonghua
School of Materials Science & Engineering, Beijing Institute of Technology Beijing 100081 China
School of Mechatronical Engineering, Beijing Institute of Technology Beijing 100081 China.
Chem Sci. 2022 May 30;13(25):7475-7481. doi: 10.1039/d2sc01933g. eCollection 2022 Jun 29.
Alkynes are widely used in chemistry, medicine and materials science. Here we demonstrate a transition-metal and photocatalyst-free inverse Sonogashira coupling reaction between iodoalkynes and (hetero)arenes or alkenes under visible-light irradiation. Mechanistic and computational studies suggest that iodoalkynes can be directly activated by visible light irradiation, and an excited state iodoalkyne acted as an "alkynyl radical synthetic equivalent", reacting with a series of C(sp)-H bonds for coupling products. This work should open new windows in radical chemistry and alkynylation method.
炔烃在化学、医学和材料科学中有着广泛的应用。在此，我们展示了在可见光照射下，碘代炔烃与（杂）芳烃或烯烃之间的一种无过渡金属和光催化剂的逆Sonogashira偶联反应。机理和计算研究表明，碘代炔烃可通过可见光照射直接活化，激发态碘代炔烃作为“炔基自由基合成等效物”，与一系列C(sp)-H键反应生成偶联产物。这项工作将为自由基化学和炔基化方法打开新的窗口。
