Synthetic utility of dizinc reagents derived from 1,4-diiodo- and 1,4-dibromooctafluorobutane

• The preparation of (solvent)nBrZn(CF2)4ZnBr(solvent)n is reported for the first time.
• An X-ray structure of (THF)2BrZn(CF2)4ZnBr(THF)2 has been reported.
• The stability of perfluoroalkyl dizinc reagents has been quantified and compared with Grignard derivatives.
• The perfluoroalkyl dizinc reagents have been used to prepare novel organics containing perfluoroalkyl ring systems.

A modified procedure to prepare [(MeCN)2Zn((CF2)4)2Zn(MeCN)2] has been developed that allows for more reproducible yields of novel organofluorines during cross-coupling protocols. Additionally, the related reagent [(diglyme)BrZn-(CF2)4-ZnBr(digylme)] has been prepared and was shown to be similarly active for [C4F8] 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.

A modified procedure to prepare [(MeCN)2Zn((CF2)4)2Zn(MeCN)2] has been developed that allows for more reproducible yields of novel organofluorines during cross-coupling protocols. Additionally, the related reagent [(diglyme)BrZn-(CF2)4-ZnBr(digylme)] has been prepared and was shown to be similarly active for [C4F8] 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.Figure optionsDownload as PowerPoint slide