Guo Shengkun, Shen Xiaoyu, Chen Xiaoyun, Yu Huaguang, Han Ying, Yan Chaoguo, Shi Yaocheng, Hou Hong, Zhu Shaoqun
School of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225009, P. R. China.
School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212005, P. R. China.
J Org Chem. 2023 Nov 17;88(22):15969-15974. doi: 10.1021/acs.joc.3c01181. Epub 2023 Oct 30.
Described herein is a photoinduced copper-catalyzed 1,2-difunctionalization of 1,3-dienes. The selenium atom radical was generated by the visible light irradiation of diselenides, triggering radical addition with 1,3-dienes to form allyl radical intermediate. Subsequent rapid / isomerization allowed for thermodynamically favorable intermediate formation and enabled copper catalyzed stereoselective functionalization with various nucleophiles.
本文描述了一种光诱导铜催化的1,3 - 二烯的1,2 - 双官能化反应。二硒醚经可见光照射产生硒原子自由基，引发其与1,3 - 二烯进行自由基加成反应，形成烯丙基自由基中间体。随后的快速异构化反应有利于形成热力学稳定的中间体，并能实现铜催化的与各种亲核试剂的立体选择性官能化反应。
