Electroreductive Olefin–Ketone Coupling,Journal of the American Chemical Society

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Electroreductive Olefin–Ketone Coupling
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-12-01 , DOI: 10.1021/jacs.0c11214
Pengfei Hu _{1,

2} , Byron K Peters _{1,

2} , Christian A Malapit _{2,

3} , Julien C Vantourout _{1,

2} , Pan Wang ₄ , Jinjun Li ₄ , Lucas Mele ₅ , Pierre-Georges Echeverria ₅ , Shelley D Minteer _{2,

3} , Phil S Baran _{1,

2}

Affiliation

A user-friendly approach is presented to sidestep the venerable Grignard addition to unactivated ketones to access tertiary alcohols by reversing the polarity of the disconnection. In this work a ketone instead acts as a nucleophile when adding to simple unactivated olefins to accomplish the same overall transformation. The scope of this coupling is broad as enabled using an electrochemical approach, and the reaction is scalable, chemoselective, and requires no precaution to exclude air or water. Multiple applications demonstrate the simplifying nature of the reaction on multistep synthesis, and mechanistic studies point to an intuitive mechanism reminiscent of other chemical reductants such as SmI2 (which cannot accomplish the same reaction).

中文翻译：

电还原烯烃-酮偶联

提出了一种用户友好的方法，通过反转断开的极性来避开古老的格氏加成法，以获取未活化酮的叔醇。在这项工作中，当加入简单的未活化烯烃以完成相同的整体转化时，酮反而充当亲核试剂。这种耦合的范围很广，因为使用电化学方法可以实现，并且反应是可扩展的、化学选择性的，并且不需要排除空气或水的预防措施。多项应用证明了多步合成反应的简化性质，机理研究指出了一种直观的机制，让人联想到其他化学还原剂，如 SmI2（不能完成相同的反应）。

更新日期：2020-12-01

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