Tetramethylpiperidine N-Oxyl (TEMPO), Phthalimide N-Oxyl (PINO), and Related N-Oxyl Species: Electrochemical Properties and Their Use in Electrocatalytic Reactions.
Tetramethylpiperidine N-Oxyl (TEMPO), Phthalimide N-Oxyl (PINO), and Related N-Oxyl Species: Electrochemical Properties and Their Use in Electrocatalytic Reactions.
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DOI：
10.1021/acs.chemrev.7b00763
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发表时间：
2018-05-09
期刊：
影响因子：
62.1
通讯作者：
Stahl SS
中科院分区：
文献类型：
--
作者：
Nutting JE;Rafiee M;Stahl SS
N-烃氧基化合物代表了广泛用作实验室和工业应用中有机分子选择性氧化催化剂的各种试剂。虽然在氧化反应中N-氧基催化剂的转换可以用各种化学计量的氧化剂来完成，但是N-氧基试剂也已经在电化学条件下在不存在化学氧化剂的情况下被广泛用作催化剂。几类N-氧基化合物在电极表面经历容易的氧化还原反应，使它们能够介导广泛的电合成反应。电化学研究还提供了对N-氧自由基化合物的化学和电化学催化的结构特性和机制的见解。本文综述了氨氧基、亚氨氧基及相关试剂的电化学性质和电催化应用，其中典型的和广泛应用的是2，2，6，6-四甲基哌啶N-氧基（克里思）和邻苯二甲酰亚胺N-氧基（PINO）。
N-oxyl compounds represent a diverse group of reagents that find widespread use as catalysts for the selective oxidation of organic molecules in both laboratory and industrial applications. While turnover of N-oxyl catalysts in oxidation reactions may be accomplished with a variety of stoichiometric oxidants, N-oxyl reagents have also been extensively used as catalysts under electrochemical conditions in the absence of chemical oxidants. Several classes of N-oxyl compounds undergo facile redox reactions at electrode surfaces, enabling them to mediate a wide range of electrosynthetic reactions. Electrochemical studies also provide insights into the structural properties and mechanisms of chemical and electrochemical catalysis by N-oxyl compounds. This review provides a comprehensive survey of the electrochemical properties and electrocatalytic applications of aminoxyls, imidoxyls, and related reagents, of which the two prototypical and widely used examples are 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) and phthalimide N-oxyl (PINO).
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