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.