A Sequential Iodination–Fluorodeiodination of the Cubane Scaffold

Organic Letters 2026 Open access

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Authors: Quentin Fevre-Renault, Masaki Hosaka, Sébastien Depienne, Robin Heinrich, Matthieu Hédouin, Hassan Oulyadi, Catherine Fressigné, Shota Nagasawa, Yoshiharu Iwabuchi, Alison M. Stuart, Bruno Linclau, Michaël De Paolis
DOI: 10.1021/acs.orglett.6c00557
Cited by: 1
References: 44

Abstract

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.

Fields of Study & Subjects

Fluorine in Organic Chemistry Vanadium and Halogenation Chemistry Oxidative Organic Chemistry Reactions

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
15
Pages
4680–4685
Publication date
2 April 2026
Language
EN