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.

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Publication Details

Journal
Organic Letters
Published
2026-04-02
DOI
https://doi.org/10.1021/acs.orglett.6c00557
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

A Sequential Iodination–Fluorodeiodination of the Cubane Scaffold

Shota Nagasawa, Sébastien Depienne, Matthieu Hédouin, Bruno Linclau et al.
Organic Letters
Fluorine in Organic Chemistry
article

A Sequential Iodination–Fluorodeiodination of the Cubane Scaffold

Shota Nagasawa, Sébastien Depienne, Matthieu Hédouin, Bruno Linclau, Alison M. Stuart, Hassan Oulyadi, Catherine Fressigné, Quentin Fevre-Renault, Robin Heinrich, Michaël De Paolis, Masaki Hosaka, Yoshiharu Iwabuchi
article en

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.

Organic LettersVol. 28(15)
Centre National de la Recherche Scientifique (FR), University of Leicester (GB), Tohoku University (JP), Ghent University (BE), Normandie Université (FR), Laboratoire de recherche en cardiovasculaire, métabolisme, diabétologie et nutrition (FR), Université de Rouen Normandie (FR), Institut National des Sciences Appliquées Rouen Normandie (FR)
Agence Nationale de la Recherche, Fonds Wetenschappelijk Onderzoek, Centre National de la Recherche Scientifique, Université de Rouen, Institut National des Sciences Appliquées Rouen, Région Normandie, European Regional Development Fund
Openalex Percentile: Top 38%
Fluorine in Organic Chemistry
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