85237-65-6

Usage

Uses

Used in Photocatalysis Industry:
2-(4-FLUOROPHENYL)-5-METHYLPYRIDINE is used as a ligand for the preparation of Ir(III) photocatalysts. These photocatalysts are valuable in various applications, such as solar energy conversion and environmental remediation, due to their ability to absorb light and facilitate chemical reactions.
In the field of photocatalysis, 2-(4-FLUOROPHENYL)-5-METHYLPYRIDINE plays a crucial role in enhancing the performance of Ir(III) complexes. The presence of the fluorophenyl group and the methyl group on the pyridine ring can influence the electronic properties and stability of the resulting complexes, making them more effective in photocatalytic processes. This allows for improved efficiency in converting light energy into chemical energy and promoting reactions that can address environmental and energy-related challenges.

InChI:InChI=1/C12H10FN/c1-9-2-7-12(14-8-9)10-3-5-11(13)6-4-10/h2-8H,1H3

Upstream product

• 78-85-3 2-methylpropenal 
• 26031-63-0 1-(2-(4-fluorophenyl)-2-oxoethyl)pyridine-1-ium bromide 
• 403-29-2 2-bromo-4'-fluoroacetophenone 
• 3510-66-5 2-Bromo-5-methylpyridine 
• 1765-93-1 4-fluoroboronic acid 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 18368-64-4 2-chloro-5-methylpyridine 

Downstream Products

• 945267-62-9 5-(bromomethyl)-2-(4-fluorophenyl)pyridine 
• 945267-61-8 C₄₂H₃₆F₃N₃O₃ 
• 808142-89-4 bis-(μ)-chloro-tetrakis(5-methyl-2-(4-fluorophenyl)-pyridinato-C²,N)-diiridium(III) 
• 1258844-08-4 Pt(II)(5-methyl-2-(4-fluorophenyl)-pyridine)(5-methyl-2-(4-fluorophenyl)-pyridine(-1H))Cl 

Relevant academic research and scientific papers

Picomole-Scale Transition Metal Electrocatalysis Screening Platform for Discovery of Mild C–C Coupling and C–H Arylation through in Situ Anodically Generated Cationic Pd

Development of new transition-metal-catalyzed electrochemistry promises to improve overall synthetic efficiency. Here, we describe the first integrated platform for online screening of electrochemical transition-metal catalysis. It utilizes the intrinsic electrochemical capabilities of nanoelectrospray ionization mass spectrometry (nano-ESI-MS) and picomole-scale anodic corrosion of a Pd electrode to generate and evaluate highly efficient cationic catalysts for mild electrocatalysis. We demonstrate the power of the novel electrocatalysis platform by (1) identifying electrolytic Pd-catalyzed Suzuki coupling at room temperature, (2) discovering Pd-catalyzed electrochemical C–H arylation in the absence of external oxidant or additive, (3) developing electrolyzed Suzuki coupling/C–H arylation cascades, and (4) achieving late-stage functionalization of two drug molecules by the newly developed mild electrocatalytic C–H arylation. More importantly, the scale-up reactions confirm that new electrochemical pathways discovered by nano-ESI can be implemented under the conventional electrolytic reaction conditions. This approach enables in situ mechanistic studies by capturing various intermediates including transient transition metal species by MS, and thus uncovering the critical role of anodically generated cationic Pd catalyst in promoting otherwise sluggish transmetalation in C–H arylation. The anodically generated cationic Pd with superior catalytic efficiency and novel online electrochemical screening platform hold great potential for discovering mild transition-metal-catalyzed reactions.

Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation

Substantial effort is currently being devoted to obtaining photoredox catalysts with high redox power. Yet, it remains challenging to apply the currently established methods to the activation of bonds with high bond dissociation energy and to substrates with high reduction potentials. Herein, we introduce a novel photocatalytic strategy for the activation of inert substituted arenes for aryl borylation by using thiolate as a catalyst. This catalytic system exhibits strong reducing ability and engages non-activated Caryl–F, Caryl–X, Caryl–O, Caryl–N, and Caryl–S bonds in productive radical borylation reactions, thus expanding the available aryl radical precursor scope. Despite its high reducing power, the method has a broad substrate scope and good functional-group tolerance. Spectroscopic investigations and control experiments suggest the formation of a charge-transfer complex as the key step to activate the substrates.

Highly Fluorinated Ir(III)-2,2′:6′,2″-Terpyridine-Phenylpyridine-X Complexes via Selective C-F Activation: Robust Photocatalysts for Solar Fuel Generation and Photoredox Catalysis

A series of fluorinated Ir(III)-terpyridine-phenylpyridine-X (X = anionic monodentate ligand) complexes were synthesized by selective C-F activation, whereby perfluorinated phenylpyridines were readily complexed. The combination of fluorinated phenylpyridine ligands with an electron-rich tri-tert-butyl terpyridine ligand generates a "push-pull" force on the electrons upon excitation, imparting significant enhancements to the stability, electrochemical, and photophysical properties of the complexes. Application of the complexes as photosensitizers for photocatalytic generation of hydrogen from water and as redox photocatalysts for decarboxylative fluorination of several carboxylic acids showcases the performance of the complexes in highly coordinating solvents, in some cases exceeding that of the leading photosensitizers. Changes in the photophysical properties and the nature of the excited states are observed as the compounds increase in fluorination as well as upon exchange of the ancillary chloride ligand to a cyanide. These changes in the excited states have been corroborated using density functional theory modeling.

Synthesis of facial cyclometalated iridium(iii) complexes triggered by tripodal ligands

The tripodal ligands composed of the 1,3,5-trisubstituted cyclohexyl moiety as a molecular scaffold and 2-phenylpyridyl moieties as a coordination site were designed. The homoleptic cyclometalated fac-Ir(C^N)3 complexes could be obtained by the reaction of IrCl3·nH2O with the designed tripodal ligands. The single crystal X-ray structure determination confirmed the fac configuration and a distorted octahedral geometry with three intramolecular cyclometalated 2-phenylpyridyl ligands surrounding the iridium metal center. Also, the cyclohexyl scaffold was found to serve as a flexible scaffold to induce the fac configuration. The thus-obtained homoleptic cyclometalated fac-Ir(C^N)3 complexes exhibited a broad emission band in the emission spectra at 298 K.

Hydrodefluorinations by low-valent niobium catalyst

Catalytic hydrodefluorinations of organofluorine compounds by low-valent niobium catalyst were developed. In the presence of niobium(V) chloride (typically, 5 mol%), fluorobenzenes, α,α,α-trifluorotoluenes and (trifluoromethyl)pyridines were hydrodefluorinated with lithium aluminum hydride to give the corresponding benzenes, toluenes and methylpyridines in good yields, respectively.

Accelerated luminophore discovery through combinatorial synthesis

A method for accelerating the discovery of ionic luminophores using combinatorial techniques is reported. The photophysical properties of the resulting transition-metal-based chromophores were compared against a series of analogous, traditionally prepared species. The strong overlap between these two sets confirms the identity of the parallel synthesis products and supports the truthfulness of the combinatorial results. Further support for the combinatorial method comes from the adherence of these complexes to the energy gap law. The relationship between the structure of a complex and its photophysical properties was also considered, and static DFT calculations were used to assess whether it is feasible to predict the luminescent behavior of novel materials.