A new nucleophilic fluorine-18 labeling method for aliphatic mesylates: Reaction in ionic liquids shows tolerance for water
A new nucleophilic fluorine-18 labeling method for aliphatic mesylates: Reaction in ionic liquids shows tolerance for water
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DOI：
10.1016/s0969-8051(03)00017-9
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发表时间：
2003-05-01
影响因子：
3.1
通讯作者：
Chi, DY
中科院分区：
文献类型：
--
作者：
Kim, DW;Choe, YS;Chi, DY
以离子液体为反应介质，用O-18（p，n）[F-18]F反应得到的F-18亲核取代某些卤代和甲磺酰氧基烷烃成为相应的[F-18]氟代烷烃，是一种新的F-18标记方法。在各种离子液体中，1-丁基-3-甲基咪唑三氟甲磺酸盐（[bmim][OTf]）在Cs2 CO 3的存在下，给出了最高的放射化学产率。该方法快速且特别方便，因为[F-18]氟化物的水溶液可以直接加入到反应介质中，避免了目前使用的放射性同位素方法通常需要的仔细干燥。作为一个模型反应，[F-18]取代2-（3-甲磺酰氧基丙氧基）萘[1]，在120 ℃下反应5-10 min，在优化条件下，以93+/-1.2%（n=3）的放化产率得到相应的[F-18]氟产物。因此，我们预计，这种方法将是非常有用的标记各种分子与[F-18]氟化物在一个方便的方式。(C)2003年爱思唯尔公司All rights reserved.
Nucleophilic [F-18]fluorination of some halo- and mesyloxyalkanes to the corresponding [F-18]fluoroalkanes with fluoride-18 obtained from an O-18(p,n) [F-18]F reaction, using an ionic liquid as a reaction medium, has been studied as a new method for fluorine-18 labeling. Of the various ionic liquids, 1-butyl-3-methylimidazolium triflate ([bmim][OTf]) in the presence of Cs2CO3, gave the highest radiochemical yields. This method is rapid and particularly convenient because [F-18]fluoride in H2O can be added directly to the reaction media, obviating the careful drying that is typically required for currently used radiofluorination methods. As a model reaction, [F-18]fluorination of 2-(3-methanesulfonyloxypropoxy)naphthalene [1] was found to provide the corresponding [F-18]fluoro product in 93+/-1.2% (n=3) radiochemical yield, after reaction at 120 degreesC for 5-10 min under optimized conditions. Thus, we anticipate that this method will be very useful in the labeling of various molecules with [F-18]fluoride in a convenient manner. (C) 2003 Elsevier Inc. All rights reserved.