225916-39-2

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-FLUOROPHENYL)-5,5-DIMETHYL-1,3,2-DIOXABORINANE is used as a key intermediate in the synthesis of various pharmaceuticals due to its ability to participate in cross-coupling reactions, enabling the creation of a wide range of medicinal compounds with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 2-(4-FLUOROPHENYL)-5,5-DIMETHYL-1,3,2-DIOXABORINANE is utilized as a building block for the development of new agrochemicals, contributing to the synthesis of molecules with pesticidal or herbicidal activities, which are essential for crop protection.
Used in Materials Science:
2-(4-FLUOROPHENYL)-5,5-DIMETHYL-1,3,2-DIOXABORINANE is employed as a component in the production of advanced materials, taking advantage of its reactivity and stability to create materials with unique electronic, optical, or mechanical properties for various applications.
Used in Electronic Materials Production:
2-(4-FLUOROPHENYL)-5,5-DIMETHYL-1,3,2-DIOXABORINANE is used as a precursor in the development of electronic materials, such as semiconductors or conductive polymers, where its integration can enhance the performance of electronic devices or contribute to the creation of new types of electronic components.
Used in Catalysis:
2-(4-FLUOROPHENYL)-5,5-DIMETHYL-1,3,2-DIOXABORINANE is applied as a reagent in catalytic processes, where it can influence the rate of chemical reactions, potentially leading to more efficient and selective synthetic routes in various chemical industries.
Used in Research and Development:
In the realm of scientific research and development, 2-(4-FLUOROPHENYL)-5,5-DIMETHYL-1,3,2-DIOXABORINANE is used as a tool to explore new chemical reactions and mechanisms, aiding in the discovery of innovative synthetic methods and the advancement of chemical knowledge.

InChI:InChI=1/C11H14BFO2/c1-11(2)7-14-12(15-8-11)9-3-5-10(13)6-4-9/h3-6H,7-8H2,1-2H3

Upstream product

• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 33756-42-2 tri-p-fluorophenylstibine 
• 1765-93-1 4-fluoroboronic acid 
• 67-56-1 methanol 
• 10294-34-5 boron trichloride 
• 668987-38-0 5,5-dimethyl-1,3,2-dioxaborinane 
• 72358-72-6 methanesulfonic acid 4-fluorophenyl ester 
• 7541-20-0 O-(4-fluorophenyl)-N,N-dimethylcarbamate 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 448-59-9 tris(4-fluorophenyl)boroxine 
• 1194-02-1 4-fluorobenzonitrile 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 31685-21-9 (4-fluorophenyl)dichloroborane 
• 57186-57-9 2-methoxy-5,5,-dimethy-1,3,2-dioxaborinane 

Downstream Products

• 225916-40-5 3,8-bis(4-fluorophenyl)-1,10-phenanthroline 
• 456-22-4 4-Fluorobenzoic acid 
• 872094-35-4 (R)-(-)-11-acetoxy-2-(4-fluorophenyl)-10-methoxyapomorphine 
• 398-24-3 4-fluoro-4'-nitro-1,1'-biphenyl 
• 1079398-05-2 C₁₅H₁₁F₃ 
• 553631-05-3 tert-butyl 4-hydroxy-4-(4-fluorophenyl)-1-piperidinecarboxylate 
• 3888-64-0 1-butyl p-fluorobenzoate 
• 324-74-3 4-fluoro-biphenyl 
• 1325593-76-7 1-(4-fluorophenyl)-1-(naphthalen-2-yl)ethanol 
• 39768-95-1 (4-Fluoro-phenyl)-(4-methoxy-phenyl)-phenyl-methanol 
• 1496-36-2 1-(4-fluorophenyl)cyclohexan-1-ol 
• 402-44-8 4-Fluorobenzotrifluoride 
• 883874-84-8 2-chloro-4-(4-fluorophenyl)pyridine 
• 179380-99-5 7-chloro-4-(4-fluorophenyl)quinoline 

Relevant academic research and scientific papers

Nickel-Catalyzed Regioselective Alkenylarylation of γ,δ-Alkenyl Ketones via Carbonyl Coordination

We disclose a nickel-catalyzed reaction, which enabled us to difunctionalize unactivated γ,δ-alkenes in ketones with alkenyl triflates and arylboronic esters. The reaction was made feasible by the use of 5-chloro-8-hydroxyquinoline as a ligand along with

Ni-Catalyzed Borylation of Aryl Sulfoxides

A nickel/N-heterocyclic carbene (NHC) catalytic system has been developed for the borylation of aryl sulfoxides with B2(neop)2 (neop=neopentyl glycolato). A wide range of aryl sulfoxides with different electronic and steric properties were converted into the corresponding arylboronic esters in good yields. The regioselective borylation of unsymmetric diaryl sulfoxides was also feasible leading to borylation of the sterically less encumbered aryl substituent. Competition experiments demonstrated that an electron-deficient aryl moiety reacts preferentially. The origin of the selectivity in the Ni-catalyzed borylation of electronically biased unsymmetrical diaryl sulfoxide lies in the oxidative addition step of the catalytic cycle, as oxidative addition of methoxyphenyl 4-(trifluoromethyl)phenyl sulfoxide to the Ni(0) complex occurs selectively to give the structurally characterized complex trans-[Ni(ICy)2(4-CF3-C6H4){(SO)-4-MeO-C6H4}] 4. For complex 5, the isomer trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I was structurally characterized in which the phenyl sulfinyl ligand is bound via the oxygen atom to nickel. In solution, the complex trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I is in equilibrium with the S-bonded isomer trans-[Ni(ICy)2(C6H5)(SOC6H5)] 5, as shown by NMR spectroscopy. DFT calculations reveal that these isomers are separated by a mere 0.3 kJ/mol (M06/def2-TZVP-level of theory) and connected via a transition state trans-[Ni(ICy)2(C6H5)(η2-{SO}-C6H5)], which lies only 10.8 kcal/mol above 5.

Synthesis of arylboronates via the Pd-catalyzed desulfitative coupling reaction of sodium arylsulfinates with bis(pinacolato)diboron

The desulfitative borylation reaction of sodium arylsulfinates with bis(pinacolato)diboron or bis(neopentylglycolato)diboron under palladium catalysis has been developed, allowing selective C-B bond formation to give arylboronates with a range of functional groups in moderate to good yields under mild reaction conditions. A gram-scale preparation as well as the cascade Suzuki-Miyaura cross-coupling of arylboronates demonstrated the potential practical utility in organic synthesis.

Ruthenium-Catalyzed Carbonylative Coupling of Anilines with Organoboranes by the Cleavage of Neutral Aryl C-N Bond

Herein, we report the first ruthenium-catalyzed Suzuki-type carbonylative reaction of electronically neutral anilines via C(aryl)-N bond cleavage. Without any ligand and base, diaryl ketones can be obtained in moderate to high yields by using Ru3/su

Ruthenium-Catalyzed Reductive Arylation of N-(2-Pyridinyl)amides with Isopropanol and Arylboronate Esters

A new three-component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2-pyridinyl (Py) directing group, is described. The N-Py-amide substrates are readily prepared from carboxylic acids and PyNH2, and the resulting N-Py-1-arylalkanamine reaction products are easily transformed into the corresponding chlorides by substitution of the HN-Py group with HCl. The 1-aryl-1-chloroalkane products allow substitution and cross-coupling reactions. Therefore, a general protocol for the transformation of carboxylic acids into a variety of functionalities is obtained. The Py-NH2 by-product can be recycled.

Transition-Metal-Free ipso-Trifluoromethylthiolation of Lithium Aryl Boronates

A transition-metal-free direct trifluoromethylthiolation of the ipso-carbon of lithium aryl boronates with trifluoromethanesulfenate under mild conditions was described. In addition, late-stage site-selective C-H borylation/trifluoromethylation and C-Cl b

Ruthenium-Catalyzed C-H Arylation and Alkenylation of Furfural Imines with Boronates

A Ru0-catalyzed direct C-H arylation and alkenylation of furfural imines with aryl- or alkenyl-boronates, in the presence of benzylideneacetone as a sacrificial hydride acceptor, is disclosed. This reaction provides access, after hydrolysis, to C3-arylated or vinylated furfural derivatives, and thus valorizes these relevant building-blocks obtained from lignocellulosic biomass. This approach, involving C-H activation by a Ru0/RuII, cycle offers several advantages, notably simple, mild and neutral reaction conditions.

Ruthenium-Catalyzed Ortho C-H Arylation of Aromatic Nitriles with Arylboronates and Observation of Partial Para Arylation

Ruthenium-catalyzed C-H arylation of aromatic nitriles with arylboronates is described. The use of RuH2(CO){P(4-MeC6H4)3}3 as a catalyst provided higher yields of the ortho arylation products than the

Selective Monoarylation of Aromatic Ketones and Esters via Cleavage of Aromatic Carbon-Heteroatom Bonds by Trialkylphosphine Ruthenium Catalysts

We report here the ruthenium-catalyzed selective monoarylation of aromatic ketones bearing two ortho carbon-heteroatom (O or N) bonds. Under the newly developed catalyst system consisting of RuHCl(CO)(PiPr3)2, CsF, and sty

Syntheses of RuHCl(CO)(PAr3)3 and RuH2(CO)(PAr3)3 Containing various triarylphosphines and their use for arylation of sterically congested aromatic C-H bonds

A series of ruthenium complexes, RuHCl(CO)(PAr3)3 and RuH2(CO)(PAr3)3, containing various triarylphosphines were synthesized. Screening of these complexes as catalysts for direct arylation of sterically congested ortho C-H bonds of aromatic ketones improved the yields of the arylation products.