Hydrogen Bond Directed Photocatalytic Hydrodefluorination: Overcoming Electronic Control was written by Khaled, Mohammad B.;El Mokadem, Roukaya K.;Weaver, Jimmie D.. And the article was included in Journal of the American Chemical Society in 2017.Category: pyridine-derivatives The following contents are mentioned in the article:
The photocatalytic C-F functionalization of highly fluorinated arenes is a powerful method for accessing functionalized multifluorinated arenes. The decisive step in the determining regioselectivity in fluorine functionalization is fluoride fragmentation from the radical anion of the multifluorinated arene. To date, the availability of regioisomers has been dictated by the innate electronics of the fluorinated arene, limiting the synthetic utility of the chem. This study investigates the remarkable ability of a strategically located hydrogen bond to transcend the normal regioselectivity of the C-F functionalization event. A significant rate acceleration is addnl. observed for hydrodefluorination of fluorines that can undergo intramol. hydrogen bonds that form 5-8-membered cycles with moderately acidic N-H’s. The hydrogen bond is expected to facilitate the fragmentation not only by bending the C-F bond of the radical anion out of planarity but also by increasing the exothermicity of the fluoride extrusion step through protonation of the naked fluoride. Finally, the synthetic utility of the method is demonstrated in an expedited synthesis of the trifluorinated α-Ph acetic acid derivative required for the com. synthesis of Januvia, an antidiabetic drug. This represents the first synthesis of a com. important multifluorinated arene via a defluorination strategy and is significantly shorter than the current strategy. This study involved multiple reactions and reactants, such as 2,3,4,5,6-Perfluoropyridine (cas: 700-16-3Category: pyridine-derivatives).
2,3,4,5,6-Perfluoropyridine (cas: 700-16-3) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Category: pyridine-derivatives