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通过阳极生成氧羰基自由基实现取代内酯的经济、绿色、安全路线。

Economical, Green, and Safe Route Towards Substituted Lactones by Anodic Generation of Oxycarbonyl Radicals.

机构信息

Department of Pharmaceutical, Chemical and Environmental Sciences, Faculty of Engineering and Science, University of Greenwich, Chatham Maritime, Chatham, Kent, ME4 4TB, UK.

出版信息

Angew Chem Int Ed Engl. 2019 Nov 4;58(45):16115-16118. doi: 10.1002/anie.201909922. Epub 2019 Sep 25.

Abstract

A new electrochemical methodology has been developed for the generation of oxycarbonyl radicals under mild and green conditions from readily available hemioxalate salts. Mono- and multi-functionalised γ-butyrolactones were synthesised through exo-cyclisation of these oxycarbonyl radicals with an alkene, followed by the sp -sp capture of the newly formed carbon-centred radical. The synthesis of functionalised valerolactone derivatives was also achieved, demonstrating the versatility of the newly developed methodology. This represents a viable synthetic route towards pharmaceutically important fragments and further demonstrates the practicality of electrosynthesis as a green and economical method to activate small organic molecules.

摘要

现已开发出一种新的电化学方法,可在温和、绿色的条件下,从易得的羟乙二酸盐生成氧羰基自由基。这些氧羰基自由基与烯烃发生外环化,随后新形成的碳中心自由基发生 sp-sp 捕获,从而合成了单官能和多官能化的γ-丁内酯。还实现了功能化戊内酯衍生物的合成,展示了新开发方法的多功能性。这代表了一种可行的合成途径,可用于获得具有重要药用价值的片段,进一步证明了电合成作为一种绿色、经济的方法来激活小分子的实用性。

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