5291-88-3

Upstream product

• 67-56-1 methanol 
• 773-82-0 Pentafluorobenzonitrile 
• 124-41-4 sodium methylate 
• 141-52-6 sodium ethanolate 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 1825-61-2 Trimethylmethoxysilane 
• 827-15-6 1,2,3,4,5-pentafluoro-6-iodobenzene 
• 20925-85-3 pentachlorobenzonitrile 
• 344-04-7 bromopentafluorobenzene 
• 344-07-0 1-chloro-2,3,4,5,6-pentafluorobenzene 
• 653-37-2 perfluorobenzaldehyde 

Downstream Products

• 144717-67-9 trans-[Pt(H)(FHF)(PCy₃)2] 

Relevant academic research and scientific papers

Mechanism of Oxidative Activation of Fluorinated Aromatic Compounds by N-Bridged Diiron-Phthalocyanine: What Determines the Reactivity?

The biodegradation of compounds with C?F bonds is challenging due to the fact that these bonds are stronger than the C?H bond in methane. In this work, results on the unprecedented reactivity of a biomimetic model complex that contains an N-bridged diiron-phthalocyanine are presented; this model complex is shown to react with perfluorinated arenes under addition of H2O2 effectively. To get mechanistic insight into this unusual reactivity, detailed density functional theory calculations on the mechanism of C6F6 activation by an iron(IV)-oxo active species of the N-bridged diiron phthalocyanine system were performed. Our studies show that the reaction proceeds through a rate-determining electrophilic C?O addition reaction followed by a 1,2-fluoride shift to give the ketone product, which can further rearrange to the phenol. A thermochemical analysis shows that the weakest C?F bond is the aliphatic C?F bond in the ketone intermediate. The oxidative defluorination of perfluoroaromatics is demonstrated to proceed through a completely different mechanism compared to that of aromatic C?H hydroxylation by iron(IV)-oxo intermediates such as cytochrome P450 Compound I.

Structural Variations in the Dithiadiazolyl Radicals p-ROC6F4CNSSN (R = Me, Et, nPr, nBu): A Case Study of Reversible and Irreversible Phase Transitions in p-EtOC6F4CNSSN

The 4′-alkoxy-tetrafluorophenyl dithiadiazolyls, ROC6F4CNSSN [R = Me (1), Et (2), nPr (3), nBu(4)] all adopt cis-oid dimers in the solid state. The methoxy derivative 1 adopts a π-stacked AA'AA' motif, whereas p

Constructing a catalytic cycle for c-f to c-x (x = o, s, n) bond transformation based on gold-mediated ligand nucleophilic attack

A tricoordinated gold(I) chloride complex, tBuXantphosAuCl, supported by a sterically bulky 9,9-dimethyl-4,5-bis(di-Tert-butylphosphino)xanthene ligand (tBuXantphos) was synthesized. This complex features a remarkably longer Au?Cl bond length [2.632(1) ?] than bicoordinated linear gold complexes (2.27-2.30 ?) and tricoordinated XantphosAuCl [2.462(1) ?]. Single-crystal Xray diffraction analysis of a cocrystal of tBuXantphosAuCl and pentafluoronitrobenzene (PFNB) and UV-vis spectroscopic titration experiments revealed the existence of an anion-φ interaction between the Cl anion ligand and PFNB. Stoichiometric reaction between PFNB and tBuXantphosAuOtBu, after replacement of Cl by a more nucleophilic tBuO anion ligand, showed higher reactivity and para selectivity in the transformation of C-F to C-OtBu bond, distinctively different from that when only KOtBu was used (ortho selectivity) under the identical condition. Mechanistic studies including density functional theory calculations suggested a gold-mediated nucleophilic ligand attack of the C?F bond pathway via an SNAr process. On the basis of these results, using trimethylsilyl derivatives TMS-X (X = OMe, SEt, NEt) as the nucleophilic ligand source and the fluorine acceptor, catalytic transformation of the C-F bond of aromatic substrates to the C-X (X = O, S, N) bond was achieved with tBuXantphosAuCl as the catalyst (up to 20 turnover numbers).

Synthesis of fluorinated indazoles through ANRORC-like rearrangement of 1,2,4-oxadiazoles with hydrazine

A series of 6-substituted fluorinated indazoles has been obtained through an ANRORC-like rearrangement (Addition of Nucleophile, Ring-Opening and Ring-Closure) of 5-tetrafluorophenyl-1,2,4-oxadiazoles with hydrazine. The initial addition of the bidentate

Quinoline-3-carboxylic acid derivatives

Compounds of formula (I): STR1 (in which R1 is alkoxy, R is alkyl, haloalkyl, alkylamino, cycloalkyl or optionally substituted phenyl, X is chlorine or fluorine and Y is selected from certain specific heterocycles) have excellent antibacterial activity. They may be prepared by introducing the group represented by Y into the corresponding compound in which Y is replaced by a halogen atom.