Electrochemical Selective Oxidative Functionalization of Caffeine,Advanced Synthesis & Catalysis

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Electrochemical Selective Oxidative Functionalization of Caffeine
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-01-27 , DOI: 10.1002/adsc.201901170
Xing‐An Liang ₁ , Dingdong Liu ₁ , He Sun ₁ , Chongyu Jiang ₁ , Hong Chen ₁ , Linbin Niu ₁ , Karuna Mahato ₁ , Takfaoui Abdelilah ₁ , Heng Zhang ₁ , Aiwen Lei ₁

Affiliation

Direct electrochemical oxidative functionalization of caffeine under metal‐free and external‐oxidant‐free conditions was achieved. Nucleophiles such as various substituted pyrazoles, alcohols, and sodium trifluoromethanesulfonate can be utilized with high diastereoselectivity for the dearomatizative functionalization of caffeine. In addition, selective C2 functionalization of caffeine has also been realized with the modification of solvent and reaction time. A gram‐scale experiment demonstrates the potential application in the derivatization of caffeine.

中文翻译：

咖啡因的电化学选择性氧化功能化

在不含金属和不含外部氧化剂的条件下，实现了咖啡因的直接电化学氧化功能化。亲核试剂，例如各种取代的吡唑，醇和三氟甲磺酸钠，可以以非对映高选择性用于咖啡因的脱芳香化功能。另外，还通过改变溶剂和反应时间实现了咖啡因的选择性C2功能化。克级实验证明了咖啡因衍生化的潜在应用。

更新日期：2020-01-29

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