Fluorine Transfer to Alkyl Radicals,Journal of the American Chemical Society

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Fluorine Transfer to Alkyl Radicals
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2012-02-22 , DOI: 10.1021/ja211679v
Montserrat Rueda-Becerril ₁ , Claire Chatalova Sazepin ₁ , Joe C. T. Leung ₁ , Tulin Okbinoglu ₁ , Pierre Kennepohl ₁ , Jean-François Paquin ₂ , Glenn M. Sammis ₁

Affiliation

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(-) or F(+)). Radical methods, while potentially attractive as a complementary approach, are hindered by a paucity of safe sources of atomic fluorine (F(•)). 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.

中文翻译：

氟转移到烷基自由基

随着含氟药物的重要性不断提高，有机化合物选择性氟化新合成技术的发展也在增加。可能适用于药物合成的传统方法依赖于使用离子形式的氟（F(-) 或 F(+)）。激进的方法虽然作为一种补充方法具有潜在吸引力，但由于缺乏安全的原子氟 (F(•)) 来源而受到阻碍。已开发出一种新的烷基氟化方法，该方法利用试剂 N-氟苯磺酰亚胺作为氟转移剂到烷基自由基。这种方法适用于广泛的烷基自由基，包括伯、仲、叔、苄基和杂原子稳定的自由基。此外，计算表明，含氟离子试剂可能是将这种方法进一步扩展到极性反应介质的候选者。在烷基自由基氟化中使用这些试剂有可能实现强大的新转化，否则将需要多个合成步骤。

更新日期：2012-02-22

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