14547-85-4

Upstream product

• 108-88-3 toluene 
• 1198288-63-9 4,5,6,7,8-pentafluoro-6-nitro-1-oxaspiro[2.5]octa-4,7-diene 
• 602-94-8 Pentafluorobenzoic acid 
• 325142-81-2 4,4,5,5-tetramethyl-2-(2,3,4,5,6-pentafluorophenyl)-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Gold-Catalyzed Direct Oxidative Arylation with Boron Coupling Partners

An efficient synthesis of biaryls through a gold-catalyzed oxidative cross-coupling of arenes with strong electron-deprived aryl boronates is presented herein. Regio- and chemocontrol are achieved by the selective activation of these coupling partners by gold at different oxidation states. Under reaction conditions devoid of basic additives or directing groups, the role of acetato ligand as an internal base has been revealed as a key parameter for expanding the reaction scope in these transformations.

Pd-catalyzed decarboxylative cross-coupling of perfluorobenzoic acids with simple arenes

Using a Pd/Ag bimetallic system, arylations of simple arenes with perfluorobenzoic acids have been achieved by decarboxylative C-H bond functionalization, providing the desired cross-coupling products in moderate to good yields. These straightforward protocols provide new and efficient methods for the synthesis of fluorobiphenyl scaffolds under simple and mild conditions.

Pentafluorophenylation of aromatic compounds with 4,5,6,7,8-pentafluoro-6- nitro-1-oxaspiro[2.5]octa-4,7-diene

4,5,6,7,8-Pentafluoro-6-nitro-1-oxaspiro[2.5]octa-4,7-diene reacts with arenes in the presence of AlCl3 to give pentafluorobiphenyls.

Fluorinated biphenyls from aromatic arylations with pentafluorobenzenediazonium and related cations. Competition between arylation and azo coupling

High yields of the mixed perfluorinated biaryls (C6F5-Ar) are obtained by the catalytic dediazonlatlon of the pentafluorobenzenediazonium salt (C6F5N2+BF4-) in acetonitrile solutions containing various aromatic substrates (ArH) together with small amounts of iodide salts. Activated (electron-rich) as well as deactivated (electron-poor) arenes are successfully pentafluorophenylated by this method. The arylation is distinct from the azo coupling of the same substrates, which takes place in the absence of the iodide catalyst and yields the corresponding diazene (C6F5N=N-Ar) as product. The catalytic role of iodide, and the isomeric product distributions obtained with this procedure indicate that the arylation proceeds via the pentafluorophenyl radical in a efficient homolytic chain process. Since azo coupling involves electrophilic aromatic substitution of electron-rich ArH by C6F5N2+, the two competing pathways are distinct and do not have reactive intermediates in common.

Thermal (iodide) and photoinduced electron-transfer catalysis in biaryl synthesis via aromatic arylations with diazonium salts

The dediazoniative arylation of various aromatic hydrocarbons (Ar'H) with diazonium salts (ArN2+) in acetonitrile can be readily effected to biaryls (Ar-Ar') in high yields, simply by the addition of small (catalytic) amounts of sodium iodide. [In the absence of Ar'H, the competitive iodination to ArI is nearly quantitative.] Iodide catalysis of biaryl formation is efficiently mediated by aryl radicals (Ar') that participate in an efficient homolytic chain process in which ArN2+ acts as a 1-electron oxidant. The complex kinetics of such an electron-transfer chain or ETC process (Scheme I) is quantitatively verified by computer simulation of the Ar'H-dependent (a) competition between arylation vs iodination and (b) catalytic efficiency of iodide. using the GEAR algorithms. ETC catalysis also pertains to the alternative photochemical procedure for arylation (in the absence of iodide), in which the deliberate irradiation of the charge-transfer band of the precursor complex (ArN2+, Ar'H) initiates the same homolytic chain arylation. The latter underscores the mechanistic generality of the ETC formulation for various types of catalytic dediazoniations of aromatic diazonium salts.

Reactions of pentafluorophenylxenon(II) hexafluoroarsenate (+)(-) with aromatic compounds

Pentafluorophenylxenon(II) hexafluoroarsenate (+)(-) reacts (MeCN, 20 deg C) with aromatic compounds C6H5X (X=CH3, F, CF3, NO2 and CN), yielding isomeric mixtures of polyfluorinated biphenyls XC6H4C6F5.When X=I, iodopentafluorobenzene is formed in addition, whereas trimethylsilylbenzene (X=SiMe3) is only converted to C6H5C6F5 and C6F5H.These results are compared with the data for the radical pentafluorophenylation and fluorination reactions of the corresponding aromatic compounds with XeF2.Polyfluoroaromatic compounds C6F6, C6F5H, C6F5I, C6F5CN and C6F5SiMe3 do not react with (+)(-) under the same conditions.

Pentafluorophenylation of Aromatics with Pentafluorophenyl Perfluoro- and Polyfluoroalkanesulfonates. A Photoinduced Electron-Transfer Cation Diradical Coupling Process

Irradiation of pentafluorophenyl perfluoro- and polyfluoroalkanesulfonates 1 with arenes, aromatic ethers, pyrroles, indoles, and phenols results in the corresponding pentafluorophenylated aromatic compounds.An electron-transfer mechanism is proposed.