Efficient Radical Oxygenation of α-Iodocarboxylic Acid Derivatives

N Kihara, C Ollivier, P Renaud

Index: Kihara, Nobuhiro; Ollivier, Cyril; Renaud, Philippe Organic Letters, 1999 , vol. 1, # 9 p. 1419 - 1422

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Citation Number: 22

Abstract

Treatment of α-iodocarboxylic acid derivatives with 2 equiv of triethylborane under oxygen atmosphere gives the corresponding α-hydroxy acid derivatives. This method is based on an iodine atom transfer from the ethyl radical, generated by the reaction of triethylborane and oxygen, with the α-iodocarbonyl compound. It offers several advantages over classical ionic substitution reactions: no elimination product is observed, tertiary iodides are efficiently ...