Fluorine Transfer to Alkyl Radicals

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• 作者：Montserrat Rueda-Becerril ; Claire Chatalova Sazepin ; Joe C. T. Leung ; Tulin Okbinoglu ; Pierre Kennepohl ; Jean-Fran莽ois Paquin ; Glenn M. Sammis
• 刊名：The Journal of the American Chemical Society
• 出版年：2012
• 出版时间：March 7, 2012
• 年：2012
• 卷：134
• 期：9
• 页码：4026-4029
• 全文大小：274K
• 年卷期：v.134,no.9(March 7, 2012)
• ISSN：1520-5126

文摘

The development of new synthetic technologies for the selective fluorination of organic compounds has increased with the escalating importance of fluorine-containing pharmaceuticals. Traditional methods potentially applicable to drug synthesis rely on the use of ionic forms of fluorine (F^{鈥?/sup> or F+). Radical methods, while potentially attractive as a complementary approach, are hindered by a paucity of safe sources of atomic fluorine (F鈥?/sup>). A new approach to alkyl fluorination has been developed that utilizes the reagent N-fluorobenzenesulfonimide as a fluorine transfer agent to alkyl radicals. This approach is successful for a broad range of alkyl radicals, including primary, secondary, tertiary, benzylic, and heteroatom-stabilized radicals. Furthermore, calculations reveal that fluorine-containing ionic reagents are likely candidates for further expansion of this approach to polar reaction media. The use of these reagents in alkyl radical fluorination has the potential to enable powerful new transformations that otherwise would take multiple synthetic steps.}