Anhydrous Tetramethylammonium Fluoride for Room-Temperature SNAr Fluorination was written by Schimler, Sydonie D.;Ryan, Sarah J.;Bland, Douglas C.;Anderson, John E.;Sanford, Melanie S.. And the article was included in Journal of Organic Chemistry in 2015.Reference of 3939-12-6 This article mentions the following:
This paper describes the room-temperature SNAr fluorination of aryl halides and nitroarenes using anhydrous tetramethylammonium fluoride (NMe4F). This reagent effectively converts aryl-X (X = Cl, Br, I, NO2, OTf) to aryl-F under mild conditions (often room temperature). Substrates for this reaction include electron-deficient heteroaromatics (22 examples) and arenes (5 examples). The relative rates of the reactions vary with X as well as with the structure of the substrate. However, in general, substrates bearing X = NO2 or Br react fastest. In all cases examined, the yields of these reactions are comparable to or better than those obtained with CsF at elevated temperatures (i.e., more traditional halex fluorination conditions). The reactions also afford comparable yields on scales ranging from 100 mg to 10 g. A cost anal. is presented, which shows that fluorination with NMe4F is generally more cost-effective than fluorination with CsF. In the experiment, the researchers used many compounds, for example, 6-Fluoronicotinonitrile (cas: 3939-12-6Reference of 3939-12-6).
6-Fluoronicotinonitrile (cas: 3939-12-6) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Reference of 3939-12-6