A Sequential Iodination–Fluorodeiodination of the Cubane Scaffold

The synthesis of fluorinated cubane derivatives is described
via
a two-step cubane iodination–fluorodeiodination sequence. The
conversion of iodocubane into fluorocubane was found to be possible
by using Selectfluor, thus avoiding the use of hazardous xenon difluoride
and allowing fluorocubane synthesis using standard equipment. In addition,
with cubane iodination typically achieved via iododecarboxylation
chemistries, we also describe an advance in cubane iodination chemistry
with the successful conversion of the commercially available dimethyl
cubane 1,4-diester into its ‘ortho’-iodinated product
using photoinduced iodination, allowing the preparation of the corresponding
fluorocubane 1,4-diester.