While there have been extensive studies in trifluoromethylation reactions by metal mediated processes, the addition of repeating difluoromethylene groups has been far less studied. While procedures to symmetrically disubstituted fluoroalkyl chains and fluoroalkyl-containing ring systems have been disclosed, a complementary route to unsymmetrical disubstituted chain derivatives remains challenging. Here, we provide a route to the novel α-bromo- ω-silyl fluoroalkylated reagents for the construction of arylated fluoroalkyl bromide building blocks. The isolable [(phen)Ag(CF<sub>2</sub>)<sub>n</sub>Br] intermediates can be prepared from the silyl reagents and respective ligand in good yield. These silver reagents are capable of transferring both the phenanthroline ligand and the fluoroalkyl bromide chain to copper iodide, eliminating the need for a preligated copper salt precursor. The respective copper species can either be isolated or generated in situ for further reactions with electron deficient or electron rich aryl iodides to assemble the targeted building blocks under mild conditions. This synthetic pathway is not only compatible with various chain lengths, but tolerant of many functional groups.

Novel route to arylated fluoroalkyl bromide building blocks through α-bromo-ω-silyl disubstituted perfluoroalkanes

253rd National Meeting (2017)

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