456-24-6Relevant articles and documents
Method for pipeline continuous fluorination with fluorine salt as fluorine source
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Paragraph 0056-0061; 0094-0096, (2021/10/27)
The method comprises the following steps: dissolving a fluorine salt in an aqueous polar aprotic solvent as reaction liquid A, dissolving an aryl (heterocyclic) chloride in a polar aprotic solvent as reaction liquid B, and reacting a polar aprotic solvent in the reaction liquid A with a polar aprotic solvent of the reaction liquid B. The reaction medium consisting of the preheated reaction liquid A and the preheated reaction liquid B enters the reaction coil for a fluorination reaction, and the resulting product from the reaction coil is subjected to post-treatment to obtain the product. The method has the characteristics of no need of adding a phase transfer catalyst, continuous production, low production cost and the like.
Tetramethylammonium Fluoride Alcohol Adducts for SNAr Fluorination
Bland, Douglas C.,Lee, So Jeong,Morales-Colón, Mariá T.,Sanford, Melanie S.,Scott, Peter J. H.,See, Yi Yang
supporting information, p. 4493 - 4498 (2021/06/28)
Nucleophilic aromatic fluorination (SNAr) is among the most common methods for the formation of C(sp2)-F bonds. Despite many recent advances, a long-standing limitation of these transformations is the requirement for rigorously dry, aprotic conditions to maintain the nucleophilicity of fluoride and suppress the generation of side products. This report addresses this challenge by leveraging tetramethylammonium fluoride alcohol adducts (Me4NF·ROH) as fluoride sources for SNAr fluorination. Through systematic tuning of the alcohol substituent (R), tetramethylammonium fluoride tert-amyl alcohol (Me4NF·t-AmylOH) was identified as an inexpensive, practical, and bench-stable reagent for SNAr fluorination under mild and convenient conditions (80 °C in DMSO, without the requirement for drying of reagents or solvent). A substrate scope of more than 50 (hetero) aryl halides and nitroarene electrophiles is demonstrated.
Synthesis and characterization of 2-pyridylsulfur pentafluorides
Kanishchev, Oleksandr S.,Dolbier, William R.
supporting information, p. 280 - 284 (2015/04/21)
Current approaches to prepare SF5-substituted heterocycles during the synthesis of targeted heterocyclic compounds require the use of SF5-functionalized aryl or alkyne reagents or SF5Cl as a source of the SF5 functional group. Herein we report that excess oxidative fluorination of 2,2' -dipyridyl disulfide with a KF/Cl2 /MeCN system leads to the formation of thirteen new 2-pyridylsulfur chlorotetrafluorides (2-SF4Cl-pyridines). These molecules are found to undergo further chlorine-fluorine exchange reactions by treatment with silver(I) fluoride enabling ready access to a series of ten new substituted 2-pyridylsulfur pentafluorides (2-SF5-pyridines). This is the first preparatively simple and readily scalable example of the transformation of an existing heterocyclic sulfur functionality to prepare SF5-substituted heterocycles.
