Tredwell Matthew, Gouverneur Véronique
University of Oxford, Chemistry Research laboratory, 12, Mansfield Road, Oxford, UK OX1 3TA.
Org Biomol Chem. 2006 Jan 7;4(1):26-32. doi: 10.1039/b513399h. Epub 2005 Nov 23.
The fluorination of organosilanes with the silyl groups directly attached or adjacent to an aryl or alkenyl group has been only very recently examined despite the fact that the corresponding fluorinated products are synthetically useful building blocks. In these reactions, the silyl group enhances the reactivity of the pi-nucleophile and controls the sense of regiochemistry upon addition of the electrophilic source of fluorine. These reactions take advantage of the beta effect of the silicon-carbon bond and recent results from the literature revealed that this chemistry allows for the preparation of a variety of novel fluorinated building blocks including enantio-enriched derivatives.
尽管相应的氟化产物是合成中有用的结构单元，但直到最近才开始研究与芳基或烯基直接相连或相邻的甲硅烷基的有机硅烷的氟化反应。在这些反应中，甲硅烷基增强了π-亲核试剂的反应性，并在添加亲电氟源时控制区域化学的方向。这些反应利用了硅-碳键的β效应，并且文献中的最新结果表明，这种化学方法可以制备各种新型氟化结构单元，包括对映体富集的衍生物。
