The First Organosilver(III) Fluoride, [PPh 4 ][(CF 3 ) 3 AgF]
| Autor: | Babil Menjón, Miguel Baya, Antonio Martín, Jesús Orduna, Daniel Joven-Sancho |
|---|---|
| Přispěvatelé: | Ministerio de Ciencia, Innovación y Universidades (España), Agencia Estatal de Investigación (España), Gobierno de Aragón |
| Rok vydání: | 2020 |
| Předmět: |
Trifluoromethyl
010405 organic chemistry Trifluoromethylation Organic Chemistry General Chemistry 010402 general chemistry 01 natural sciences Medicinal chemistry Catalysis Dissociation (chemistry) 0104 chemical sciences chemistry.chemical_compound Hydrolysis chemistry Nucleophile Chemical stability Multistage mass spectrometry Fluoride |
| Zdroj: | Digital.CSIC. Repositorio Institucional del CSIC instname |
| ISSN: | 1521-3765 0947-6539 |
| DOI: | 10.1002/chem.201905771 |
| Popis: | Organosilver(III) fluoride complexes have been assigned a key role in different fluorination processes. To the best of our knowledge, however, none of them seem to have been isolated or even detected thus far. Here we report on the successful synthesis of the trifluoromethyl derivative [PPh4][(CF3)3AgF], which has been isolated in high yield. The thermodynamic stability of the Ag−F bond is shown by calculation and demonstrated by multistage mass spectrometry (MSn) under collision‐induced dissociation (CID) conditions. Nevertheless, the substantial elongation found in the Ag−F bond (X‐ray) is correlated with a marked nucleophilic character of the terminal F ligand. This Ag−F bond is, in fact, quite reactive: it suffers hydrolysis and is also solvolyzed by thiols. This work was supported by the Spanish MICIU/FEDER (Project PGC2018‐094749‐B‐I00) and the Gobierno de Aragón (Group E17_R17). The Instituto de Biocomputación y Física de Sistemas Complejos (BIFI) and the Centro de Supercomputación de Galicia (CESGA) are acknowledged for allocation of computational resources. D.J.‐S. also thanks the Spanish MICIU for a grant (BES‐2016‐078732). |
| Databáze: | OpenAIRE |
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