An experimentalist's guide to electrosynthesis: the Shono oxidation
An experimentalist's guide to electrosynthesis: the Shono oxidation
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DOI：
10.1016/j.tetlet.2015.10.090
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发表时间：
2015-12-09
影响因子：
1.8
通讯作者：
Jones, Alan M.
中科院分区：
文献类型：
--
作者：
Alfonso-Suarez, Paulino;Kolliopoulos, Athanasios V.;Jones, Alan M.
电合成是一种不需要使用化学试剂或保护基团就能使有机分子功能化的强大方法，但它在合成中的应用并不广泛。在这项研究中，我们研究了叔酰胺的Shono氧化（与酰胺氮原子相邻的C-H键的电化学官能化），证明了进行循环伏安法，改变电压和每摩尔电荷，选择电解质和电极材料的价值。我们揭开神秘的过程，以证明一个简单的氧化电位之间的关系，和所需的电荷转移，这提供了一个高的转换到所需的α-甲氧基化的产品使用未分割的实验室。(C)2015爱思唯尔有限公司版权所有。
Electrosynthesis is a powerful method to functionalise organic molecules without the need to use chemical reagents or protecting groups, yet it is not widely used in synthesis. In this study, we investigated the Shono oxidation of a tertiary amide (electrochemical functionalisation of a C-H bond adjacent to an amide nitrogen atom), demonstrating the value of performing cyclic voltammetry, varying voltage and charge per mole, selection of electrolyte and electrode material. We demystify the process to demonstrate a simple relationship between oxidation potential, and charge transfer required, which affords a high conversion to the desired alpha-methoxylated product using an undivided experimental cell. (C) 2015 Elsevier Ltd. All rights reserved.