cas 292621-58-0, 3-CHLORO-2,4,5,6-TETRAFLUOROBENZOYL CHLORIDE

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Hydrogen Bond Directed Photocatalytic Hydrodefluorination and Methods of Use Thereof
Methods of synthesizing compounds comprising fluorinated aryl groups are disclosed, wherein said methods utilize hydrogen bond directed photocatalytic hydrodefluorination.
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(2021/01/22)

Hydrogen Bond Directed Photocatalytic Hydrodefluorination: Overcoming Electronic Control
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 chemistry. 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 additionally observed for hydrodefluorination of fluorines that can undergo intramolecular 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-phenyl acetic acid derivative required for the commercial synthesis of Januvia, an antidiabetic drug. This represents the first synthesis of a commercially important multifluorinated arene via a defluorination strategy and is significantly shorter than the current strategy.
Khaled, Mohammad B.,El Mokadem, Roukaya K.,Weaver, Jimmie D.
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p. 13092 - 13101
(2017/09/26)

Chemical Properties

Boiling Point: 189.8 ºC at 760 mmHg
Flash Point:68.6 ºC
Density: 1.707 g/cm³
Vapor Pressure: 0.561mmHg at 25°C
Refractive Index: 1.4898
Sensitive: Moisture Sensitive
PSA: 17.07000
LogP: 3.27540

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Chemical Properties

Boiling Point: 189.8 ºC at 760 mmHg

Flash Point:68.6 ºC

Density: 1.707 g/cm³

Vapor Pressure: 0.561mmHg at 25°C

Refractive Index: 1.4898

Sensitive: Moisture Sensitive

PSA: 17.07000

LogP: 3.27540

Global suppliers and manufacturers of 292621-58-0total 13 suppliers on LookChem

Article Database

292621-58-0

Articles about 292621-58-0Total 2 be found

More Articles about upstream products of 292621-58-0

Chemical Properties

Boiling Point: 189.8 ºC at 760 mmHg

Flash Point:68.6 ºC

Density: 1.707 g/cm3

Vapor Pressure: 0.561mmHg at 25°C

Refractive Index: 1.4898

Sensitive: Moisture Sensitive

PSA: 17.07000

LogP: 3.27540

Global suppliers and manufacturers of 292621-58-0total 13 suppliers on LookChem

Density: 1.707 g/cm³