Iodine in Modern Oxidation Catalysis

Abstract

This review discusses the origins of iodine-mediated oxidation catalysis and gives a comprehensive overview on this young field of research. The focus is set on oxidative C-X bond-forming reactions starting from two unfunctionalized C-H and X-H bonds. In addition, iodine-mediated oxidative domino reactions will be discussed.

α-Acetoxyarone synthesis via iodine-catalyzed and tert-butyl hydroperoxide-mediateded self-intermolecular oxidative coupling of aryl ketones

“…The process begins with the formation of α-iodoaryl ketones 5 and 6 via iodination of aryl ketones with I 2 and TBHP [24–25]. An I − /I 2 redox cycle promotes tert -butoxyl and tert -butylperoxyl radical formation from TBHP [26–28]. In the presence of TBHP and I 2 , α-iodoaryl ketones 5 and 6 are oxidized to a 1,2-diketone intermediate 7 and an α-carbonyl radical 9 , which can be further transformed to tert -butyl perester 8 and cation 11 [22].…”

Recent advances in catalytic silylation of hydroxyl‐bearing compounds: A green technique for protection of alcohols using Si–O bond formations

“…[83] During recent decades, we have witnessed great interest in iodine catalysis because of the latest developments in halogen-bond catalysis. [84] There are some specific refinements on the model despite the fact that the introduction of silyl protecting groups on alcohols usually occurs through the traditional path of a trialkylchlorosilane or a trialkylsilyl triflate and a base. [85] In this sense, one can mention the application of trialkylsilyl chloride, NMI as the base and a nucleophilic catalyst.…”

Recent Advances in the I2-Catalyzed C-H Bond Functionalizations

“…α-酮酰胺是重要的结构单元, 在天然产物和生物医药中广泛存在, 其结构单元在功能 团转化中用途广泛 [74] . 相比于之前的报道 [75] , 该方法采 用的芳基甲基酮底物廉价易得, 且操作简单, 利于工业 化生产, 具有重要合成意义. 2016 年, Adimurthy 课题组 [87] 开发了一种吲嗪-1-羧 酸酯化合物的合成方法(Eq.…”