唐林. 1,3-二羰基化合物的区域和化学选择性氟化[J]. 信阳师范学院学报(自然科学版).
引用本文: 唐林. 1,3-二羰基化合物的区域和化学选择性氟化[J]. 信阳师范学院学报(自然科学版).
Regio- and Chemoselective Fluorination of 1,3-Dicarbonyl Compounds[J]. Journal of Xinyang Normal University (Natural Science Edition).
Citation: Regio- and Chemoselective Fluorination of 1,3-Dicarbonyl Compounds[J]. Journal of Xinyang Normal University (Natural Science Edition).

1,3-二羰基化合物的区域和化学选择性氟化

Regio- and Chemoselective Fluorination of 1,3-Dicarbonyl Compounds

  • 摘要: 以廉价易得的1-氯甲基-4-氟-1,4-重氮化二环2.2.2辛烷双(四氟硼酸)盐为氟源,以1,3-二羰基化合物为反应原料在乙醇和水的混合溶剂中可以高效地发生α-位点的区域选择性氟代反应;通过对氟源的用量和反应时间的调控,可以高化学选择性地构建一系列2-单氟代和2,2-双氟代的1,3-二羰基目标化合物.该反应无需过渡金属催化剂、碱性添加剂以及额外的氧化,在室温条件下即可通过单电子氧化还原历程完成,且可进行克规模级别的放大量生产,提供了一种方便而实用的自由基氟化新方法.

     

    Abstract: Highly regioselective α-fluorination of 1,3-dicarbonyl compounds could proceed smoothly by virtue of 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo2.2.2octane bis(tetrafluoroborate) as the fluorine source in the mixed solvent of ethanol and water. By adjusting the amount of the fluorine source and reaction time, the desired 2-fluoro- and 2,2-difluoro-1,3-dicarbonyl compounds could also be efficiently constructed with an excellent chemoselectivity. The reaction readily took place via a single electron transfer process at room temperature without any transition-metal catalyst, alkaline additive or additional oxidant and could be applicated in gram-scale synthesis, which features a convenient and practical free-radical fluorination.

     

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