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Selective electrochemical generation of benzylic radicals enabled by ferrocene-based electron-transfer mediators†
Chemical Science ( IF 7.6 ) Pub Date : 2017-11-06 00:00:00 , DOI: 10.1039/c7sc04032f
Alastair J J Lennox 1 , Jordan E Nutting 1 , Shannon S Stahl 1
Affiliation  

The generation and intermolecular functionalisation of carbon-centred radicals has broad potential synthetic utility. Herein, we show that benzylic radicals may be generated electrochemically from benzylboronate derivatives at low electrode potentials (ca. −0.3 V vs. Cp2Fe0/+) via single electron oxidation. Use of a catalytic quantity of a ferrocene-based electron-transfer mediator is crucial to achieve successful radical functionalisation and avoid undesirable side reactions arising from direct electrochemical oxidation or from the use of stoichiometric ferrocenium-based oxidants.

中文翻译:

基于二茂铁的电子转移介体选择性电化学生成苄基自由基†

以碳为中心的自由基的产生和分子间功能化具有广泛的潜在合成用途。在此,我们表明,在低电极电势( ca. -0.3 V vs. Cp 2 Fe 0/+)下,苄基硼酸酯衍生物可以通过单电子氧化以电化学方式产生苄基自由基。使用催化量的二茂铁基电子转移介体对于成功实现自由基官能化并避免因直接电化学氧化或使用化学计量的二茂铁基氧化剂引起的不良副反应至关重要。
更新日期:2017-11-06
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