Ambiphilic properties of SF5CF2CF2Br derived perfluorinated radical in addition reactions across carbon-carbon double bonds.
Ambiphilic properties of SF5CF2CF2Br derived perfluorinated radical in addition reactions across carbon-carbon double bonds.
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DOI：
10.1021/acs.orglett.5b00268
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发表时间：
2015-02
期刊：
影响因子：
5.2
通讯作者：
P. Dudziński;Andrej V Matsnev;J. Thrasher;G. Haufe
中科院分区：
文献类型：
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作者：
P. Dudziński;Andrej V Matsnev;J. Thrasher;G. Haufe
五氟磺胺基（SF5）的特殊性质引起了有机化学家的关注。虽然已经合成了许多SF5取代的化合物，但直接引入SF5(CF2)n基团的研究仍然很少。我们的研究揭示了SF5CF2CF2自由基的双亲性。富电子或缺电子烯烃的加成反应得益于其亲电性或亲核性。因此，易于获得的SF5CF2CF2Br被证明是引入这种全氟化部分的有前途和通用的构建块。
The extraordinary properties of the pentafluorosulfanyl (SF5) group attract attention of organic chemists. While numerous SF5-substituted compounds have been synthesized, the direct introduction of SF5(CF2)n moieties has remained almost unexplored. Our investigations revealed the ambiphilic character of the SF5CF2CF2 radical. Addition reactions to electron-rich or electron-deficient alkenes profit either from its electrophilic or nucleophilic properties. Thus, the readily available SF5CF2CF2Br proved to be a promising and versatile building block for the introduction of this perfluorinated moiety.