化学
循环伏安法
电子顺磁共振
电化学
傅里叶变换红外光谱
光化学
溴化物
有机化学
化学工程
物理化学
电极
核磁共振
物理
工程类
作者
Meng Xue,Tao Pan,Zhichao Shao,Wenxuan Wang,Hu Li,Lixing Zhao,Xin Zhou,Yuexia Zhang
出处
期刊:Chemsuschem
[Wiley]
日期:2024-01-16
卷期号:17 (10)
被引量:2
标识
DOI:10.1002/cssc.202400028
摘要
Abstract New methods and strategies for the direct oxidation of benzylic C−H bonds are highly desirable, owing to the importance of ketone motifs in significant organic transformations and the synthesis of valuable molecules, including pharmaceuticals, pesticides, and fine chemicals. Herein, we describe an electrochemical benzylic C−H oxidation strategy for the synthesis of ketones using MeOH as an oxygen source. Inexpensive and safe KBr serves as both an electrolyte and a bromide radical precursor in the reaction. This transformation also offers several advantages such as mild conditions, broad functional group tolerance, and operational simplicity. Mechanistic investigations by control experiments, radical scavenging experiments, electron paramagnetic resonance (EPR), kinetic studies, cyclic voltammetry (CV), and in‐situ Fourier transform infrared (FTIR) spectroscopy support a pathway involving the formation and transformation of benzyl methyl ether via hydrogen atom transfer (HAT) and single‐electron transfer (SET). The practical application of our strategy is highlighted by the successful synthesis of five pharmaceuticals, namely lenperone, melperone, diphenhydramine, cinnarizine, and flunarizine.
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