Song Huanhuan, Li Jingwen, Zhang Yinbin, Chen Ke, Liu Le, Zhang Junjie, Duan Xin-Hua, Hu Mingyou
Xi'an Key Laboratory of Sustainable Energy Material Chemistry, School of Chemistry, Engineering Research Center of Energy Storage Materials and Devices, Ministry of Education, Xi'an Jiaotong University, Xi'an 710049, China.
Department of Oncology, Second Affiliated Hospital of Xi'an Jiaotong University, Xi'an 710049, China.
J Org Chem. 2023 Aug 18;88(16):12013-12023. doi: 10.1021/acs.joc.3c01336. Epub 2023 Aug 7.
Difluoromethylated heterocyclic compounds have found broad applications in numerous bioactive molecules. Herein, we report photoredox catalysis-induced direct C-H difluoromethylation of heterocycles by using bis(difluoromethyl) pentacoordinate phosphorane (PPh(CFH), ) as the reagent. A variety of heterocycles, such as quinoxalin-2(1)-one, thiophene, indole, and coumarin, are readily tailored with a difluoromethyl group. The method is featured as transition-metal-free by using an organic compound Erythrosin B as the catalyst and O as the oxidant.
二氟甲基化杂环化合物在众多生物活性分子中有着广泛的应用。在此，我们报道了以双（二氟甲基）五配位磷烷（PPh(CFH)₂）为试剂，通过光氧化还原催化实现杂环化合物的直接C-H二氟甲基化反应。多种杂环化合物，如喹喔啉-2(1H)-酮、噻吩、吲哚和香豆素，都能很容易地引入二氟甲基。该方法以有机化合物赤藓红B为催化剂、氧气为氧化剂，具有无过渡金属的特点。
