448-59-9

Usage

Uses

Used in Organic Synthesis:
2,4,6-TRIS(4-FLUOROPHENYL)BOROXIN is used as a reagent in cross-coupling reactions for the formation of carbon-carbon bonds. Its high reactivity and the presence of fluorine atoms in its structure make it particularly useful in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,4,6-TRIS(4-FLUOROPHENYL)BOROXIN is used as a building block for the development of new drugs. Its unique structure and reactivity allow for the creation of novel compounds with potential therapeutic applications.
Used in Material Science:
2,4,6-TRIS(4-FLUOROPHENYL)BOROXIN is also utilized in material science for the synthesis of advanced materials with specific properties. Its ability to form complex structures can be harnessed to create materials with tailored characteristics for various applications, such as electronics, coatings, and polymers.
Used in Research and Development:
In the field of research and development, 2,4,6-TRIS(4-FLUOROPHENYL)BOROXIN serves as a key compound for exploring new reaction pathways and understanding the fundamental aspects of organic chemistry. Its unique properties make it an essential tool for scientists working on the cutting edge of chemical synthesis and molecular design.

InChI:InChI=1/C18H12B3F3O3/c22-16-7-1-13(2-8-16)19-25-20(14-3-9-17(23)10-4-14)27-21(26-19)15-5-11-18(24)12-6-15/h1-12H

Upstream product

• 1765-93-1 4-fluoroboronic acid 
• 688-74-4 boric acid tributyl ester 
• 352-13-6 4-flourophenylmagnesium bromide 
• 121-43-7 Trimethyl borate 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 85107-53-5 ortho-(N,N-dimethylaminomethyl)phenylboronic acid 

Downstream Products

• 352-33-0 1-Chloro-4-fluorobenzene 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 414910-20-6 (R)-2-(4-Fluoro-phenyl)-4-oxo-piperidine-1-carboxylic acid benzyl ester 
• 78494-26-5 3-(4-fluorophenyl)cyclohexan-1-one 
• 28396-55-6 2-(4-fluorophenyl)naphthalene 
• 147022-23-9 (4-fluorophenyl)(1-naphthyl)methanol 
• 61495-15-6 3-(4-fluorophenyl)-1,2-dihydronaphthalene 
• 1224738-32-2 N-benzyl-3,4-dihydro-4-(4-fluorophenyl)quinolin-2(1H)-one 
• 1224738-67-3 3,4-dihydro-4-(4-fluorophenyl)coumarin 
• 1224738-59-3 N-benzyl-4-(4-fluorophenyl)pyrrolidin-2-one 
• 395-21-1 1-(4-fluorophenyl)-1-phenylethylene 
• 1229227-05-7 C₁₅H₁₄FNO 
• 1309582-67-9 N-[(R)-(4-fluorophenyl)(phenyl)methyl]-N'-[(S)-(4-fluorophenyl)(phenyl)methyl]sulfamide 
• 1309582-59-9 N,N'-sulfonyl bis-[(S)-(4-fluorophenyl)(phenyl)methanamine] 

Relevant academic research and scientific papers

Nickel(II)-Catalyzed Addition of Aryl and Heteroaryl Boroxines to the Sulfinylamine Reagent TrNSO: The Catalytic Synthesis of Sulfinamides, Sulfonimidamides, and Primary Sulfonamides

We report a redox-neutral Ni(II)-catalyzed addition of (hetero)aryl boroxines to N-sulfinyltritylamine (TrNSO). The reactions use a catalyst generated from the combination of commercial, air-stable NiCl2·(glyme) and a commercially available bipyridine lig

Copper-Catalyzed Asymmetric Arylation of N-Heteroaryl Aldimines: Elementary Step of a 1,4-Insertion

Copper complexes of monodentate phosphoramidites efficiently promote asymmetric arylation of N-azaaryl aldimines with arylboroxines. DFT calculations and experiments support an elementary step of 1,4-insertion in the reaction pathway, a step in which an aryl-copper species adds directly across four atoms of C=N?C=N in the N-azaaryl aldimines.

Rhodium-Catalyzed Enantioposition-Selective Hydroarylation of Divinylphosphine Oxides with Aryl Boroxines

The rhodium-catalyzed hydroarylation of divinylphosphine oxides (RP(O)(CH=CH2)2) with aryl boroxines ((ArBO)3) gives the corresponding monoarylation products (RP(O)(CH=CHAr)CH2CH3) in high yields. One of the two vinyl groups in the phosphine oxide undergoes oxidative arylation while the other one is reduced to an ethyl moiety. These reactions proceed with high selectivity in terms of the enantiotopic vinyl groups in the presence of (R)-DTBM-segphos/Rh to give the P-stereogenic monoarylation products with high enantioselectivity.

Unveiling the role of boroxines in metal-free carbon-carbon homologations using diazo compounds and boronic acids

By means of computational and experimental mechanistic studies the fundamental role of boroxines in the reaction between diazo compounds and boronic acids was elucidated. Consequently, a selective metal-free carbon-carbon homologation of aryl and vinyl boroxines using TMSCHN2, giving access to TMS-pinacol boronic ester products, was developed.

Palladium(II)-Catalyzed Enantioselective Synthesis of α-(Trifluoromethyl)arylmethylamines

We describe a method for the synthesis of α-(trifluoromethyl)arylmethylamines that consists of the palladium(II)-catalyzed addition of arylboroxines to imines derived from trifluoroacetaldehyde. Palladium acetate is used as a catalyst with electron-neutral or electron-rich arylboroxines, and it was found that addition of an ammonium or silver salt was crucial to promote the reaction of electron-poor boroxines. With (S)-t-Bu-PyOX as the chiral ligand, this method delivers a variety of α-trifluoromethylated amines in 57-91% yield and with greater than 92% ee in most cases.

Oxidative coupling of aryl boron reagents with sp3-carbon nucleophiles: The enolate chan–evans–lam reaction

Reported is a versatile new oxidative method for the arylation of activated methylene species. Under mild reaction conditions (RT to 40°C), Cu(OTf)2mediates the selective coupling of functionalized aryl boron species with a variety of stabilized sp3-nucleophiles. Tertiary malonates and amido esters can be employed as substrates to generate quaternary centers. Complementing either traditional cross-coupling or SNAr protocols, the transformation is chemoselective in the presence of halogen electrophiles, including aryl bromides and iodides. Substrates bearing amide, sulfonyl, and phosphonyl groups, which are not amenable to coupling under mild Hurtley-type conditions, are suitable reaction partners.

Asymmetric Synthesis of Triarylmethanes by Rhodium-Catalyzed Enantioselective Arylation of Diarylmethylamines with Arylboroxines

The reaction of racemic diarylmethylamines, (Ar1Ar2CHNR2), where Ar1 is substituted with a 2-hydroxy group, with arylboroxines (Ar3BO)3 in the presence of a chiral diene-rhodium catalyst gave high yields of chiral triarylmethanes (Ar1Ar2CH?Ar3) with high enantioselectivity (up to 97% ee). The reaction is assumed to proceed through o-quinone methide intermediates which undergo Rh-catalyzed asymmetric 1,4-addition of the arylboron reagents.

Vibrational properties of boroxine anhydride and boronate ester materials: Model systems for the diagnostic characterization of covalent organic frameworks

The vibrational characteristics of 28 different boronic acid, boroxine anhydride, and boronate ester species have been systematically investigated using a combination of experimental infrared (IR) spectroscopy and computational modeling. IR bands characteristic to each boron-containing functionality have been categorized and assigned in conjunction with density functional theory (B3LYP/6-31G(d)), with the aim of better understanding and distinguishing the vibrational characteristics of covalent organic frameworks (COFs) built from boronic acids. In several cases, vibrational assignments differ from those previously reported in the literature on boronic acid-based COFs. Vibrations commonly regarded as diagnostic for one functionality are found in regions of the IR spectrum where other functionalities also show characteristic peaks. The collective experimental and computational results reveal that several alternative bands in the IR region can be used to more diagnostically distinguish between boronic acid, boroxine anhydride, and boronate ester species. The results presented herein provide the tools for straightforward characterization of boroxine anhydride and boronate ester species using IR spectroscopy. The results can be applied to additional theoretical studies of larger COF-like assemblies as well as the analysis of other boronic-acid-based materials.

Enantioselective, nickel-catalyzed suzuki cross-coupling of quinolinium ions

Quinolinium ions are engaged in an asymmetric, Ni-catalyzed Suzuki cross-coupling to yield 2-aryl- and 2-heteroaryl-1,2-dihydroquinolines. Key to the development of this method is the use of a Ni(II) precatalyst that activates without the need for strong reductants or high temperatures. The Ni-iminium activation mode is demonstrated as an exceptionally mild pathway to generate enantioenriched products from racemic starting materials.

Diastereoselective synthesis of vicinally bis(trifluoromethylated) alkylboron compounds through successive insertions of 2,2,2-trifluorodiazoethane

The usefulness of embedded CF3 substituents within organic substructures necessitates the development of diverse methods for incorporating this functional group. A recently reported route to α-trifluoromethylated alkylboron compounds by an α-transfer mechanism has now been extended to the synthesis of unprecedented, vicinally ditrifluoromethylated alkylboron compounds in a diastereoselective fashion. The utility of these products is highlighted by conversion of the C-B bond into other functional groups.