化学
乙烯基
自由基离子
光化学
烯烃
芳基
自由基引发剂
根本歧化
电泳剂
格式化
自由基取代
激进的
反应性(心理学)
氢原子
电子转移
芳基
离子
有机化学
烷基
催化作用
歧化
聚合物
替代医学
病理
医学
聚合
作者
Cecilia M. Hendy,Gavin C. Smith,Zihao Xu,Tianquan Lian,Nathan T. Jui
摘要
We developed an effective method for reductive radical formation that utilizes the radical anion of carbon dioxide (CO2•-) as a powerful single electron reductant. Through a polarity matched hydrogen atom transfer (HAT) between an electrophilic radical and a formate salt, CO2•- formation occurs as a key element in a new radical chain reaction. Here, radical chain initiation can be performed through photochemical or thermal means, and we illustrate the ability of this approach to accomplish reductive activation of a range of substrate classes. Specifically, we employed this strategy in the intermolecular hydroarylation of unactivated alkenes with (hetero)aryl chlorides/bromides, radical deamination of arylammonium salts, aliphatic ketyl radical formation, and sulfonamide cleavage. We show that the reactivity of CO2•- with electron-poor olefins results in either single electron reduction or alkene hydrocarboxylation, where substrate reduction potentials can be utilized to predict reaction outcome.
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