Sodium-Ketyl Radical Anions by Reverse Pinacol Reaction and Their Coupling with Iodoarenes

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• 作者：Xinjun Tang ; Armido Studer
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：September 2, 2016
• 年：2016
• 卷：18
• 期：17
• 页码：4448-4450
• 全文大小：281K
• 年卷期：0
• ISSN：1523-7052

文摘

Transition-metal-free C–C bond formation between aryl iodides and pinacols is presented. Pinacols are readily transformed by deprotonation with NaH to their Na-pinacolates. C–C-bond homolysis at room temperature generates in situ the corresponding Na-ketyl radical anions which react with various aryl iodides in a homolytic aromatic substitution reaction to form tertiary Na-alcoholates. Protonation eventually provides tertiary alcohols in an unprecedented route.