Zhu Yan, Jiang Cong, Li Heng, Liu Ping, Sun Peipei
School of Chemistry and Materials Science, Jiangsu Provincial Key Laboratory of Material Cycle Processes and Pollution Control, Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Nanjing Normal University, Nanjing 210023, China.
J Org Chem. 2022 Aug 19;87(16):11031-11041. doi: 10.1021/acs.joc.2c01293. Epub 2022 Aug 2.
An efficient strategy involving electrochemical C═C double-bond cleavage and functionalization of cyclic alkenes for the synthesis of ketonitriles is described. This transformation features environmentally friendly conditions and utilizes relatively safe TMSN as the nitrogenation reagent and molecular oxygen as the oxidant. For the open-chain alkenes, the reaction gave 1,2-difunctionalized products. A wide range of cyclic alkenes and open-chain alkenes were found to be compatible, providing the corresponding ketonitriles and α-azido aromatic ketones in moderate to good yields.
本文描述了一种高效的策略,该策略涉及电化学C═C双键裂解及环烯烃官能化以合成酮腈。此转化具有环境友好的条件,并使用相对安全的TMSN作为氮化试剂,以分子氧作为氧化剂。对于开链烯烃,该反应生成1,2-双官能化产物。结果发现,多种环烯烃和开链烯烃都适用,能以中等至良好的产率提供相应的酮腈和α-叠氮基芳基酮。