79069-70-8Relevant articles and documents
Shielding Effect of Micelle for Highly Effective and Selective Monofluorination of Indoles in Water
Bora, Pranjal P.,Bihani, Manisha,Plummer, Scott,Gallou, Fabrice,Handa, Sachin
, p. 3037 - 3042 (2019/04/01)
Highly selective direct monofluorination of indoles and arenes was developed through an approach that allows site-specific solubility of substrate and fluorine source in the micelle. This approach was highly selective for a broad range of substrates with excellent functional group tolerance. Differences in binding constant and solubility of indoles and arenes in the micelle allowed the fine-tuning of selectivity. Control experiments suggested a radical pathway and provided insight into the role of micelles of the environmentally benign amphiphile PS-750-M. Dynamic light scattering experiments strongly indicated the site-specific solubility of the substrate and fluorine source. The methodology was successfully adapted to gram scale, and the E-factor established from a recycle study indicated that the process is environmentally responsible and sustainable.
Solvent-free fluorination of organic compounds using N-F reagents
Stavber, Gaj,Zupan, Marko,Stavber, Stojan
, p. 2671 - 2673 (2008/02/03)
Efficient fluorination of 1,3-dicarbonyl compounds, enol acetates of aromatic ketones, and activated aromatic compounds was achieved under solvent-free conditions using Selectfluor F-TEDA-BF4 or Accufluor NFSi.
A Novel Electrophilic Fluorination of Activated Aromatic Rings Using Acetyl Hypofluorite, Suitable also for Introducing (18)F into Benzene Nuclei
Lerman, Ori,Yitzhak, Tor,Hebel, David,Rozen, Shlomo
, p. 806 - 813 (2007/10/02)
Acetyl hypofluorite (1) is a new compound that serves as a novel electrophilic fluorinating agent.It is special in the sense that, while it is very reactive, it is still a milder reagent than other fluoroxy compounds such as CF3OF or CF3COOF.It is synthesized directly from elemental fluorine and is used without any isolation or purification.The hypofluorite 1 reacts efficiently and selectively with activated aromatic rings,particularly phenol and aniline derivatives after suitable protection of the hydroxyl and the amino groups.The net result of the reaction is partly according to classical aromatic electrophilic substitution.Unlike such a substitution, however, the electrophilic fluorine atom of 1 substitutes mainly an ortho hydrogen and only occasionally small amounts of p-fluoro derivatives are found.Evidence supports the mechanism for this aromatic fluorination as being mainly an addition-elimination one.In many cases the electrophilic aromatic fluorinations can replace the classical 60-year-old Balz-Schiemann method, which until today is probably the most used procedure.Since aromatic fluorination with 1 is a very fast reaction and since 1 is produced directly from elemental fluorine, this is probably one of the best ways for introduction of the short-living radioisotope (18)F into activated aromatic rings.This will greatly encourage the synthesis of compounds suitable for use in the rapidly developing field of positron emitting transaxial tomography, which in itself depends on the efficient and easy supply of compounds possessing positron emitting isotopes.