462-06-6Relevant articles and documents
Fluoroaromatics from arylamines, a convenient one-pot conversion using nitrosonium tetrafluoroborate
Milner
, p. 73 - 82 (1992)
A simple, novel and extremely versatile procedure has been identified for the conversion of arylamines into the corresponding arylfluorides. The amine is treated with nitrosonium tetrafluoroborate in dichloromethane and the resulting diazonium tetrafluoroborate is heated, without isolation or drying, to give the fluoroaromatic, generally in good yield. The method is applicable even to arylamines bearing carboxyl and hydroxyl substituents which give poor yields of arylfluorides under Balz-Schiemann conditions.
Cleavage of Aryl-Tin Bonds with Elemental Fluorine: Rapid Synthesis of Fluorobenzene
Adam, Michael J.,Pate, Brian D.,Ruth, Thomas J.,Berry, Joffre M.,Hall, Laurance D.
, p. 733 (1981)
Fluorobenzene has been synthesized rapidly by treatment of aryltin derivatives with F2 in CFCl3 or CCl4 at -78 to 0 deg C.
DIRECT LIQUID-PHASE FLUORINATION OF AROMATIC COMPOUNDS. NEW ADVANCES IN ELECTROPHILIC FLUORINATION
Gambaretto, G. P.,Conte, L.,Fraccaro, C.,Napoli, M.
, p. 241 (1991)
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Preparation of Fluoroarenes in One-Pot Diazotization and Fluoro-Dediazoniation of Aminoarenes Using HF or HF-Base. The Functions of Bases in the HF Solution
Fukuhara, Tsuyoshi,Sasaki, Satoshi,Yoneda, Norihiko,Suzuki, Akira
, p. 2058 - 2062 (1990)
In a one-pot diazotization of anilines followed by fluoro-dediazoniation in situ using HF or HF with bases (HF-Base) as a solvent, the diazotization stage has been found to play the most important part to yield fluoroarenes effectively.Diazotization of anilines was greatly influenced by the composition of the HF solution, and greatly enhanced by employing appropriate amounts of bases, such as pyridine.On the other hand, fluoro-dediazoniation of diazonium salts, once formed, took place very readily in HF or HF-Base to produce fluoroarenes in high yield, although such bases served to slow down the rate of decomposition of diazonium salts to some extent.
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Feng,Mamula
, p. 507 (1958)
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Speranza et al.
, p. 5583,5588 (1977)
Photochemical Sandmeyer-type Halogenation of Arenediazonium Salts
Belitz, Florian,Goo?en, Lukas J.,Manu Martínez, ángel,Schmid, Rochus,Sivendran, Nardana,Sowa Prendes, Daniel
, (2022/01/19)
Trihalide salts were found to efficiently promote photochemical dediazotizing halogenations of diazonium salts. In contrast to classical Sandmeyer reactions, no metal catalysts are required to achieve high yields and outstanding selectivities for halogena
Mechanistic studies into visible light-driven carboxylation of aryl halides/triflates by the combined use of palladium and photoredox catalysts
Caner, Joaquim,Iwasawa, Nobuharu,Martin, Ruben,Murata, Kei,Shimomaki, Katsuya,Toriumi, Naoyuki
supporting information, p. 1846 - 1853 (2021/08/13)
The reaction mechanism of palladium-catalyzed visible light-driven carboxylation of aryl halides and triflates with a photoredox catalyst was examined in detail. Experimental and theoretical studies indicated that the active species for photoredox- catalyzed reduction was cationic ArPd(II)+ species to generate nucleophilic ArPd(I) or its further reduced ArPd(0)- species, which reacted with CO2 to give carboxylic acids. Hydrodehalogenated compounds, main byproducts in this carboxylation, were thought to be generated by protonation of these reduced species.