Multi-faceted reactivity of N-fluorobenzenesulfonimide (NFSI) under mechanochemical conditions: fluorination, fluorodemethylation, sulfonylation, and amidation reactions
In the search for versatile reagents compatible with mechanochemical techniques, in this work we studied the reactivity of N-fluorobenzenesulfonimide (NFSI) by ball milling. We corroborated that, by mechanochemistry, NFSI can engage in a variety of reactions such as fluorinations, fluorodemethylatio...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2022-02-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.18.20 |
| _version_ | 1819121062768541696 |
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| author | José G. Hernández Karen J. Ardila-Fierro Dajana Barišić Hervé Geneste |
| author_facet | José G. Hernández Karen J. Ardila-Fierro Dajana Barišić Hervé Geneste |
| author_sort | José G. Hernández |
| collection | DOAJ |
| description | In the search for versatile reagents compatible with mechanochemical techniques, in this work we studied the reactivity of N-fluorobenzenesulfonimide (NFSI) by ball milling. We corroborated that, by mechanochemistry, NFSI can engage in a variety of reactions such as fluorinations, fluorodemethylations, sulfonylations, and amidations. In comparison to the protocols reported in solution, the mechanochemical reactions were accomplished in the absence of solvents, in short reaction times, and in yields comparable to or higher than their solvent-based counterparts. |
| first_indexed | 2024-12-22T06:30:35Z |
| format | Article |
| id | doaj.art-49a2626676e649ffbd7af30f97c34cd0 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-22T06:30:35Z |
| publishDate | 2022-02-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-49a2626676e649ffbd7af30f97c34cd02022-12-21T18:35:43ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972022-02-0118118218910.3762/bjoc.18.201860-5397-18-20Multi-faceted reactivity of N-fluorobenzenesulfonimide (NFSI) under mechanochemical conditions: fluorination, fluorodemethylation, sulfonylation, and amidation reactionsJosé G. Hernández0Karen J. Ardila-Fierro1Dajana Barišić2Hervé Geneste3Division of Physical Chemistry, Ruđer Bošković Institute, Bijenička c. 54, 10000 Zagreb, CroatiaDivision of Materials Chemistry, Ruđer Bošković Institute, Bijenička c. 54, 10000 Zagreb, CroatiaDivision of Physical Chemistry, Ruđer Bošković Institute, Bijenička c. 54, 10000 Zagreb, CroatiaAbbVie Deutschland GmbH & Co. KG, Neuroscience Research, D-67008 Ludwigshafen, GermanyIn the search for versatile reagents compatible with mechanochemical techniques, in this work we studied the reactivity of N-fluorobenzenesulfonimide (NFSI) by ball milling. We corroborated that, by mechanochemistry, NFSI can engage in a variety of reactions such as fluorinations, fluorodemethylations, sulfonylations, and amidations. In comparison to the protocols reported in solution, the mechanochemical reactions were accomplished in the absence of solvents, in short reaction times, and in yields comparable to or higher than their solvent-based counterparts.https://doi.org/10.3762/bjoc.18.20amidationball millfluorinationin situ monitoringmechanochemistrynfsiraman monitoringsulfonylation |
| spellingShingle | José G. Hernández Karen J. Ardila-Fierro Dajana Barišić Hervé Geneste Multi-faceted reactivity of N-fluorobenzenesulfonimide (NFSI) under mechanochemical conditions: fluorination, fluorodemethylation, sulfonylation, and amidation reactions Beilstein Journal of Organic Chemistry amidation ball mill fluorination in situ monitoring mechanochemistry nfsi raman monitoring sulfonylation |
| title | Multi-faceted reactivity of N-fluorobenzenesulfonimide (NFSI) under mechanochemical conditions: fluorination, fluorodemethylation, sulfonylation, and amidation reactions |
| title_full | Multi-faceted reactivity of N-fluorobenzenesulfonimide (NFSI) under mechanochemical conditions: fluorination, fluorodemethylation, sulfonylation, and amidation reactions |
| title_fullStr | Multi-faceted reactivity of N-fluorobenzenesulfonimide (NFSI) under mechanochemical conditions: fluorination, fluorodemethylation, sulfonylation, and amidation reactions |
| title_full_unstemmed | Multi-faceted reactivity of N-fluorobenzenesulfonimide (NFSI) under mechanochemical conditions: fluorination, fluorodemethylation, sulfonylation, and amidation reactions |
| title_short | Multi-faceted reactivity of N-fluorobenzenesulfonimide (NFSI) under mechanochemical conditions: fluorination, fluorodemethylation, sulfonylation, and amidation reactions |
| title_sort | multi faceted reactivity of n fluorobenzenesulfonimide nfsi under mechanochemical conditions fluorination fluorodemethylation sulfonylation and amidation reactions |
| topic | amidation ball mill fluorination in situ monitoring mechanochemistry nfsi raman monitoring sulfonylation |
| url | https://doi.org/10.3762/bjoc.18.20 |
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