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Concerning the Mechanism of the FeCl3-Catalyzed α-Oxyamination of Aldehydes: Evidence for a Non-SOMO Activation Pathway
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2010-07-28 , DOI: 10.1021/ja1043006 Jeffrey F Van Humbeck 1 , Scott P Simonovich , Robert R Knowles , David W C MacMillan
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2010-07-28 , DOI: 10.1021/ja1043006 Jeffrey F Van Humbeck 1 , Scott P Simonovich , Robert R Knowles , David W C MacMillan
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The mechanism of a recently reported aldehyde alpha-oxyamination reaction has been studied using a combination of kinetic, spectrometric, and spectrophotometric techniques. Most crucially, the use of a validated cyclopropane-based radical-clock substrate has demonstrated that carbon-oxygen bond formation occurs predominantly through an enamine activation manifold. The mechanistic details reported herein indicate that, as has been proposed for previously studied alcohol oxidations, complexation between TEMPO and a simple metal salt leads to electrophilic ionic reactivity.
中文翻译：
关于 FeCl3 催化的醛 α-氧化反应的机制：非 SOMO 激活途径的证据
最近报道的醛α-氧胺化反应的机理已经通过动力学、光谱和分光光度技术的组合进行了研究。最重要的是，使用经过验证的基于环丙烷的自由基时钟底物已证明碳-氧键的形成主要通过烯胺活化歧管发生。本文报道的机理细节表明，正如之前研究的醇氧化所提出的那样，TEMPO 和简单金属盐之间的络合导致亲电子离子反应性。
更新日期：2010-07-28
中文翻译：
关于 FeCl3 催化的醛 α-氧化反应的机制：非 SOMO 激活途径的证据
最近报道的醛α-氧胺化反应的机理已经通过动力学、光谱和分光光度技术的组合进行了研究。最重要的是，使用经过验证的基于环丙烷的自由基时钟底物已证明碳-氧键的形成主要通过烯胺活化歧管发生。本文报道的机理细节表明，正如之前研究的醇氧化所提出的那样，TEMPO 和简单金属盐之间的络合导致亲电子离子反应性。
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