The preparation of new dizinc reagents [(MeCN) 2 Zn((CF 2 ) n ) 2 Zn(MeCN) 2 ] (n = 3, 4, and 6) is reported. We show that the C4 reagent can readily transmetalate nickel to form a mononuclear perfluoronickelacycle. We also demonstrate that the reagents can be used to prepare novel fluoroorganics containing either perfluoroalkyl ring systems or perfluoroalkyl linked arenes under relatively mild conditions.

A number of copper reagents were compared for their effectiveness in trifluoromethylating 4-iodobiphenyl, 4-iodotoluene, and 2-iodotoluene. Yields over time were plotted in order to refine our understanding of each reagent performance, identify any bottlenecks, and provide more insight into the rates of the reactions. Interestingly, differences in reactivity were observed when a well-defined [LCuCF3] complex was employed directly or generated in situ from precursors by published reports. Relative reactivities were also found to highly dependent on the nature of the iodoarenes.

A modified procedure to prepare [(MeCN) 2 Zn((CF 2) 4) 2 Zn(MeCN) 2 ] has been developed that allows for more reproducible yields of novel organofluorines during cross-coupling protocols. Additionally, the related reagent [(diglyme)BrZn-(CF 2) 4-ZnBr(digylme)] has been prepared and was shown to be similarly active for [C 4 F 8 ] transfer to both organic and inorganic substrates. The di(zinc halide) reagent is operationally simple to prepare using inexpensive and easy to handle zinc metal.

No abstract

New difunctionalized and fluoroalkylated silyl reagents have been prepared that react with silver and copper salts to afford active catalysts that can be used to synthesize arylated fluoroalkyl bromide building blocks. It has been shown that the [(phen)Ag(CF2)nBr] intermediates 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 methodology is compatible with various chain lengths of the fluoroalkyl halide functionality.