The synthetic arena of Tetrafluoroethylation is still much less established than that of its counterparts like fluorination and trifluoromethylation, but a growing number of new methodologies and reagents are developped and led themselves to be potentially utilized in life and material sciences. For instance, tetrafluorinated sugar analogues were found to be significantly less hydrophilic than the parent carbohydrates, and thus exhibit enchanced protein-carbonhydrate binding capabilities. Modular electrophilic tetrafluoroethylating reagents have been empolyed as tools for irreversible Cysteine-Selective Protein Labeling, which explores a novel approach to thiol bio-conjugation that overcome the drawbacks of traditional methods. Moreover, the incorporation of CF2CF2 moiety as an internal perfluoroalkanediyl (IPF) fragment can be potentially used to further enhance molecular recognition within the receptor due to its unique property of "polar hydrophobicity".
The reaction protocols for Tetrafluoroethylation are practically subdivided into electrophilic,radical and nucleophilic processes, as pathways for most fluorination and fluoroalkylation.
1. Electrophilic Tetrafluoroethylation: Most recently, the group of Prof. Dr. A. Togni in ZTH Zurich and its partner in Czech Repubilic has developped and patented a series of new hypervalent iodine CF2CF2X reagents,which represent an extension of the orginal scaffolds of orginal cyclic hypervalent iodine-CF3 reagents(the so-called Togni reagents). Such eletrophilic tetrafluoroethylating reagents were prepared by the Umpolung of the corresponding fluoroalkyl silanes with the appropriate fluoroiodanes. They are displaying a unique reactivity resmebling that of their established CF3 analogues and the relatively high number of synthetically accessible CF2CF2X motifs, which offers an expedient and promising route for synthesis of tertrafluoroethlated products with potential applicaiton in the design of new drug and pesticide candidates.
2. Radical Tetrafluoroethylation: Trimethyl-(1,1,2,2-tetrafluoro-2-phenylsulfanylethyl)silane (PhS(CF2)2SiMe3,kumi4F05) was reported to be employed as a tandem radical and anion CF2CF2 synthon, and more recently (2-bromo-1,1,2,2-tetrafluoroethylsulfanyl)benzene (PhSCF2CF2Br,kumi4F12) used as a radical synthon for preparation of tetrafluoroethylated compounds. Prof. J.Hu and coworkers have,most recently,developed highly efficient methods and protocols for tertrafluoroethylation, in which Trimethyl(trifluoromethyl)silane(TMSCF3,kumi3F01) was used as a convenient source of CF2=CF2 and thus on-site preparation of Tetrafluoroethylene (TFE) was accomplished by dimerization of difluorocarbene derived from start material under mild conditions.
3. Nucleophilic Tetrafluoroethylation: Three new tetrafluoroethylating reagents(PhSO2CF2CF2R,R=SiMe3,SiEt3 and H) were developed by Prof. P.Beier and coworkers for nucleophilic tetrafluoroethylation of carbonyl compound, thus affording rare alcohols containing the CF2CF2 motif. These newly reported reagents extend the synthetic toolkit for selective introduction of tetrafluoroethyl groups by nucleophilic additions.
Our product portfolio to this field are reagents and building blocks which provide either straightforward synthetic pathway or novel and unique access to a variety of tetrafluoroethyl- and tetrafluoroethylene-containing compounds.
Tetrafluoroethylating Reagents Overview
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You can either buy our tetrafluorethylating reagents and then introduce tetrafluoroethyl group into your own desired compounds, or you can simply order the building blocks pre-loaded with tetrafluoroethyl(CF2CF2H) or tetrafluoroethylene(CF2CF2).
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