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通过碳-碳双键断裂实现环状烯烃的电化学好氧氧化和氮化,或通过开链烯烃的氧化和叠氮化实现其电化学好氧氧化和氮化。

Electrochemical Aerobic Oxygenation and Nitrogenation of Cyclic Alkenes via C═C Bond Cleavage or Oxygenation and Azidation of Open-Chain Alkenes.

作者信息

Zhu Yan, Jiang Cong, Li Heng, Liu Ping, Sun Peipei

机构信息

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.

出版信息

J Org Chem. 2022 Aug 19;87(16):11031-11041. doi: 10.1021/acs.joc.2c01293. Epub 2022 Aug 2.

Abstract

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.

摘要

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。

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