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- Hui Liu
- Service de Chimie Bio-organique et Marquage (SCBM), IBITECS, CEA Université Paris-Saclay 91191 Gif-sur-Yvette France
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- Davide Audisio
- Service de Chimie Bio-organique et Marquage (SCBM), IBITECS, CEA Université Paris-Saclay 91191 Gif-sur-Yvette France
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- Lucie Plougastel
- Service de Chimie Bio-organique et Marquage (SCBM), IBITECS, CEA Université Paris-Saclay 91191 Gif-sur-Yvette France
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- Elodie Decuypere
- Service de Chimie Bio-organique et Marquage (SCBM), IBITECS, CEA Université Paris-Saclay 91191 Gif-sur-Yvette France
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- David‐Alexandre Buisson
- Service de Chimie Bio-organique et Marquage (SCBM), IBITECS, CEA Université Paris-Saclay 91191 Gif-sur-Yvette France
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- Oleksandr Koniev
- Syndivia SAS 650 Boulevard Gonthier O'Andernach 67400 Illkirch France
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- Sergii Kolodych
- Syndivia SAS 650 Boulevard Gonthier O'Andernach 67400 Illkirch France
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- Alain Wagner
- Laboratory of Functional Chemo-Systems UMR 7199 CNRS-UdS 67401 Illkirch France
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- Mourad Elhabiri
- Laboratory of Bioorganic and Medicinal Chemistry, UMR 7509 CNRS ECPM 25, rue Becquerel 67200 Strasbourg France
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- Anna Krzyczmonik
- Turku PET Centre and Department of Chemistry University of Turku 20520 Turku Finland
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- Sarita Forsback
- Turku PET Centre and Department of Chemistry University of Turku 20520 Turku Finland
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- Olof Solin
- Turku PET Centre and Department of Chemistry University of Turku 20520 Turku Finland
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- Véronique Gouverneur
- Chemistry Research Laboratory University of Oxford 12 Mansfield Road Oxford OX1 3TA UK
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- Frédéric Taran
- Service de Chimie Bio-organique et Marquage (SCBM), IBITECS, CEA Université Paris-Saclay 91191 Gif-sur-Yvette France
書誌事項
- 公開日
- 2016-08-25
- 権利情報
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- http://onlinelibrary.wiley.com/termsAndConditions#vor
- DOI
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- 10.1002/anie.201606495
- 公開者
- Wiley
この論文をさがす
説明
<jats:title>Abstract</jats:title><jats:p>We report the synthesis and reactivity of 4‐fluorosydnones, a unique class of mesoionic dipoles displaying exquisite reactivity towards both copper‐catalyzed and strain‐promoted cycloaddition reactions with alkynes. Synthetic access to these new mesoionic compounds was granted by electrophilic fluorination of σ‐sydnone Pd<jats:sup>II</jats:sup> precursors in the presence of Selectfluor. Their reactions with terminal and cyclic alkynes were found to proceed very rapidly and selectively, affording 5‐fluoro‐1,4‐pyrazoles with bimolecular rate constants up to 10<jats:sup>4</jats:sup> <jats:sc>m</jats:sc><jats:sup>−1</jats:sup> s<jats:sup>−1</jats:sup>, surpassing those documented in the literature with cycloalkynes. Kinetic studies were carried out to unravel the mechanism of the reaction, and the value of 4‐fluorosydnones was further highlighted by successful radiolabeling with [<jats:sup>18</jats:sup>F]Selectfluor.</jats:p>
収録刊行物
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- Angewandte Chemie International Edition
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Angewandte Chemie International Edition 55 (39), 12073-12077, 2016-08-25
Wiley