214360-65-3

Usage

Uses

Used in Organic Synthesis:
4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER is used as a reagent for the formation of carbon-carbon and carbon-heteroatom bonds, which are crucial in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER is used as a key intermediate in the synthesis of various drugs. Its ability to form new bonds makes it valuable for the development of novel pharmaceutical compounds with specific therapeutic properties.
Used in Agrochemical Industry:
4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER is utilized as a building block in the creation of agrochemicals, contributing to the development of new pesticides and other agricultural chemicals that can improve crop protection and yield.
Used in Materials Science:
In the field of materials science, 4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER is employed in the synthesis of advanced materials with unique properties, such as high-performance polymers and specialty materials for various applications.
Used in Suzuki-Miyaura Cross-Coupling Reaction:
4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER is used as a nucleophile in the Suzuki-Miyaura cross-coupling reaction, a widely employed method for the formation of new carbon-carbon bonds, which is essential for the synthesis of a broad range of organic compounds, including those with potential applications in medicine, materials, and other industries.

InChI:InChI=1/C14H16BF3O3/c1-13(2)14(3,4)21-15(20-13)9-5-7-10(8-6-9)19-12(18)11(16)17/h5-8H,1-4H3

Upstream product

• 98-08-8 α,α,α-trifluorotoluene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 98-56-6 4-chlorobenzotrifluoride 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 455-13-0 4-Iodobenzotrifluoride 
• 51901-85-0 bromocatecholborane 
• 7440-66-6 zinc 
• 455-14-1 4-trifluoromethylphenylamine 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 132803-38-4 Benzenesulfonic acid 4-trifluoromethyl-phenyl ester 
• 345958-72-7 4-(trifluoromethyl)phenyl 4-methylbenzenesulfonate 
• 128796-39-4 4-trifluoromethylphenylboronic acid 

Downstream Products

• 1008756-39-5 C₂₀H₁₂F₆S 
• 1187791-58-7 2-(4-trifluoromethylphenyl)cyclopent-2-enone 
• 1234215-27-0 1-(hex-1-en-3-yl)-4-(trifluoromethyl)benzene 
• 1185842-26-5 N-[(4-trifluoromethylphenyl)(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]acetamide 
• 1185842-28-7 N-[(4-trifluoromethylphenyl)(phenyl)methyl]acetamide 
• 1373773-66-0 2,5-bis(3’-hexyl-5’-[4-(trifluoromethyl)phenyl]thiophen-2’-yl)thiazolo-[5,4-d]thiazole 
• 402-44-8 4-Fluorobenzotrifluoride 
• 1533422-41-1 C₁₃H₁₃F₆NO₄S 
• 1608482-92-3 2-(4-chloro-6-(4-(trifluoromethyl)phenyl)pyridin-2-yl)thiazole 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 1616729-57-7 2-(difluoro(4-(trifluoromethyl)phenyl)methyl)benzo[d]oxazole 
• 128814-90-4 2-(4-(trifluoromethyl)phenyl)-4H-chromen-4-one 
• 402-45-9 4-hydroxybenzotrifluoride 

Relevant academic research and scientific papers

Conclusive Evidence on the Mechanism of the Rhodium-Mediated Decyanative Borylation

The stoichiometric reactions proposed in the mechanism of the rhodium-mediated decyanative borylation have been performed and all relevant intermediates isolated and characterized including their X-ray structures. Complex RhCl{xant(PiPr2)2} (1, xant(PiPr2)2 = 9,9-dimethyl-4,5-bis(diisopropylphosphino)xanthene) reacts with bis(pinacolato)diboron (B2pin2), in benzene, to give the rhodium(III) derivative RhHCl(Bpin){xant(PiPr2)2} (4) and PhBpin. The reaction involves the oxidative addition of B2pin2 to 1 to give RhCl(Bpin)2{xant(PiPr2)2}, which eliminates ClBpin generating Rh(Bpin){xant(PiPr2)2} (2). The reaction of the latter with the solvent yields PhBpin and the monohydride RhH{xant(PiPr2)2} (6), which adds the eliminated ClBpin. Complex 4 and its catecholboryl counterpart RhHCl(Bcat){xant(PiPr2)2} (7) have also been obtained by oxidative addition of HBR2 to 1. Complex 2 is the promoter of the decyanative borylation. Thus, benzonitrile and 4-(trifluoromethyl)benzonitrile insert into the Rh-B bond of 2 to form Rh{C(R-C6H4)-NBpin}{xant(PiPr2)2} (R = H (8), p-CF3 (9)), which evolve into the aryl derivatives RhPh{xant(PiPr2)2} (3) and Rh(p-CF3-C6H4){xant(PiPr2)2} (10), as a result of the extrusion of CNBpin. The reactions of 3 and 10 with B2pin2 yield the arylBpin products and regenerate 2.

Cu-mediated: vs. Cu-free selective borylation of aryl alkyl sulfones

A Cu-catalysed borylation of aryl alkyl sulfones was developed for the high yield synthesis of versatile arylboronic esters using a readily prepared NHC-Cu catalyst. In addition, the selective cleavage of either alkyl(C)-sulfonyl or aryl(C)-sulfonyl bonds

Unreactive C-N Bond Activation of Anilines via Photoinduced Aerobic Borylation

Unreactive C-N bond activation of anilines was achieved by photoinduced aerobic borylation. A diverse range of tertiary and secondary anilines were converted to aryl boronate esters in moderate to good yields with wide functional group tolerance under simple and ambient photochemical conditions. This transformation achieved the direct and facile C-N bond activation of unreactive anilines, providing a convenient and practical route transforming widely available anilines into useful aryl boronate esters.

Palladium-catalyzed borylation of aryl bromides and chlorides using phosphatrioxa-adamantane ligands

Catalysts based on the combination of Pd(OAc)2 and the electron-deficient phosphatrioxa-adamantane ligands are described for borylation of aryl bromides and chlorides. Catalytic evaluation of a small library of phosphatrioxa-adamantane ligands provided some insights on the preferred ligand steric profile for borylation reactions. The corresponding aryl boronate esters were accessed under mild conditions (25–70 °C) and isolated in high yields (up to 96%).

Photochemical and electrochemical C-N borylation of arylhydrazines

The C-N borylation of arylhydrazine hydrochlorides with bis(pinacolato)diboron was achieved under photochemical and electrochemical conditions, respectively. This novel and scalable transformation provides two efficient and mild transition-metal-free synt

Ligand-Enabled, Iridium-Catalyzed ortho-Borylation of Fluoroarenes

A terpyridine derivative and an iridium complex catalyze the C-H borylation of a stoichiometric amount of a fluoroarene with high ortho-selectivity and tolerance of functional groups such as bromide, chloride, ester, ketone, amine, and in situ-borylated hydroxyl. Complex drug molecules such as haloperidol can be selectively borylated ortho to the F atom. The terpyridine ligand undergoes rollover cyclometalation to produce an N,N,C-coordinated iridium complex, which may either selectively borylate the fluoroarene by itself or undergo reductive elimination to produce a borylated ligand.

Evaluation of the role of graphene-based Cu(i) catalysts in borylation reactions

Carbon-supported catalysts have been considered as macromolecular ligands which modulate the activity of the metallic catalytic center. Understanding the properties and the factors that control the interactions between the metal and support allows a fine tuning of the catalyzed processes. Although huge effort has been devoted to comprehending binding energies and charge transfer for single atom noble metals, the interaction of graphenic surfaces with cheap and versatile Cu(i) salts has been scarcely studied. A methodical experimental and theoretical analysis of different carbon-based Cu(i) materials in the context of the development of an efficient, general, scalable, and sustainable borylation reaction of aliphatic and aromatic halides has been performed. We have also examined the effect of microwave (MW) radiation in the preparation of these type of materials using sustainable graphite nanoplatelets (GNP) as a support. A detailed analysis of all the possible species in solution revealed that the catalysis is mainly due to an interesting synergetic Cu2O/graphene performance, which has been corroborated by an extensive theoretical study. We demonstrated through DFT calculations at a high level of theory that graphene enhances the reactivity of the metal in Cu2O against the halide derivative favoring a radical departure from the halogen. Moreover, this material is able to stabilize radical intermediates providing unexpected pathways not observed using homogeneous Cu(i) catalysed reactions. Finally, we proved that other common carbon-based supports like carbon black, graphene oxide and reduced graphene oxide provided poorer results in the borylation process.

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF

Compound for patterning of fluorine-containing metal or electrode and organic electronic element using the same An electronic device is provided to form a fine pattern of an electrode without using a shadow mask by using the fluorinated compound as a metal or an electrode patterning material, thereby easily manufacturing a transparent display having a high light transmittance, thereby facilitating UDC application.

Engaging Ag(0) single atoms in silver(I) salts-mediated C-B and C-S coupling under visible light irradiation

Silver(I) salts were found active in the borylation and sulfenylation of aryl iodides under visible light irradiation. The optimized borylation protocol using AgF did not need any additive, operated under very mild conditions, and well tolerated a broad scope of substrates and boron sources. Formation of Ag(0) single atoms (AgSAs) during the borylation reactions was examined using high-angle annular dark field aberration-corrected scanning transmission electron microscope (HAADF AC-STEM) and electron paramagnetic resonance (EPR). The activities of the silver(I) salts were affected by the anions and could be associated with their abilities in formation of AgSAs during the reactions. Kinetic studies showed that the deiodination rate was linearly correlated with the loading of AgSAs, and hence AgSAs were the true catalytic centers for the 1e?-reduction of the C-I moieties. The oxidation state of AgSAs kept 0 in both the resting and the working states. A “work-in-tandem” mechanism involving AgSAs as the catalytic centers and AgNPs as the light absorber to achieve the borylation of aryl iodides under visible light irradiation is proposed. The current approach not only provides an alternative system for borylation and sulfenylation of aryl iodides, but also reveals a new activity of silver(I) salts involving AgSAs under visible light irradiation.

Zinc Complexes with an Ethylene-Bridged Bis(β-diketiminate) Ligand: Syntheses, Structures, and Applications as Catalysts in the Borylation of Aryl Iodides

A dinucleating bis(β-diketiminate) ligand with a flexible bridge has been employed to synthesize zinc complexes. The ligand, abbreviated H2L (H2L = N-(4-((2-((4-((2,6-diisopropylphenyl)imino)pent-2-en-2-yl)amino)ethyl)imino)pent-2-en-2-yl)-2,6-diisopropylaniline), was deprotonated with ZnEt2 to afford [LZn2Et2] (1). Reactions of 1 with 2 equiv of BnOH and nBuOH, respectively, gave access to [LZn2(OBn)2]·C6H14 (2·C6H14) and [LZn2(OnBu)2] (3). Treatment of 1 with 2 equiv of I2 in THF produced [LZn2I2(THF)2]·2THF (4·2THF). X-ray single-crystal diffraction analyses revealed that they are all heteroleptic bimetallic compounds with two metal centers being chelated by one ligand set. The structurally similar compounds 1 and 4·2THF possess approximate C2 symmetry, with two β-diketiminate units being arrayed in head-to-tail antiparallel mode. Thus, the molecular structures of 1 and 4·2THF exhibit a seesaw-like topology. The structures of 2·C6H14 and 3 are almost identical, in which two zinc atoms are shared by two ZnN2C3 six-membered rings, two Zn2ON2C2 seven-membered rings, and one Zn2O2 four-membered ring. Therefore, the metal cores of 2·C6H14 and 3 display a crownlike topology. All complexes are catalytically active for the borylation of aryl iodides with B2Pin2 (B2Pin2 = 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis(1,3,2-dioxaborolane). Complex 1 shows higher activity in comparison to 2, 3, and 4·2THF. The borylation reactions catalyzed by 1 could proceed under mild conditions and can be applied to a series of substrates with high functional group generality. This methodology thus represents a novel use of β-diketiminate zinc complexes for C-I borylation.