754226-39-6

Usage

Uses

Used in Organic Synthesis:
2-(3,4-Difluorophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane is used as a reagent for the direct arylation of heterocycles, enabling the formation of carbon-carbon bonds and the synthesis of complex organic molecules.
Used in Pharmaceutical and Agrochemical Synthesis:
2-(3,4-Difluorophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane serves as a precursor for the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides with improved efficacy and reduced side effects.
Used in Advanced Electronic Materials:
2-(3,4-Difluorophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane is used in the production of organic light-emitting diodes (OLEDs) and other electronic materials, enhancing their performance and expanding their applications in various electronic devices.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-(3,4-Difluorophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane is employed for the development of new therapeutic agents, leveraging its unique chemical properties and reactivity to create novel drug candidates with potential therapeutic benefits.
Used in Materials Science:
2-(3,4-Difluorophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane is utilized in materials science for the design and synthesis of new materials with specific properties, such as improved conductivity, stability, or biocompatibility, for various applications.
Used in Chemical Research:
2-(3,4-Difluorophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane is also employed in chemical research to explore new reaction mechanisms, develop innovative synthetic methods, and gain insights into the fundamental aspects of organic and inorganic chemistry.

Upstream product

• 348-61-8 1-bromo-3,4-difluorobenzene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 64248-58-4 1,2-difluoro-4-iodo-benzene 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 
• 455-86-7 3,4-Difluorobenzoic acid 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 367-23-7 1,2,4-trifluorobenzene 
• 367-11-3 ortho-difluorobenzene 
• 3863-11-4 3,4-difluoroaniline 

Downstream Products

• 1469858-52-3 2-(3,4-difluorophenyl)-6-(4-methoxyphenyl)-4-(2-trimethylsilanylethoxymethyl)-4,7-dihydro-1-thia-4,5-diazacyclopenta[a]pentalene 

Relevant academic research and scientific papers

Palladium-Catalyzed Decarbonylative Borylation of Carboxylic Acids: Tuning Reaction Selectivity by Computation

Decarbonylative borylation of carboxylic acids is reported. Carbon electrophiles are generated directly after reagent-enabled decarbonylation of the in situ accessible sterically-hindered acyl derivative of a carboxylic acid under catalyst controlled conditions. The scope and the potential impact of this method are demonstrated in the selective borylation of a variety of aromatics (>50 examples). This strategy was used in the late-stage derivatization of pharmaceuticals and natural products. Computations reveal the mechanistic details of the unprecedented C?O bond activation of carboxylic acids. By circumventing the challenging decarboxylation, this strategy provides a general synthetic platform to access arylpalladium species for a wide array of bond formations from abundant carboxylic acids. The study shows a powerful combination of experiment and computation to predict decarbonylation selectivity.

METHODS OF MANUFACTURING OF BORON COMPOUND WITHOUT TRANSITION METALS

The present invention refers to aryl boron compound number bath method relates to search, more particularly transition metal catalyst to a tank without the use of boron compounds number is given to the aryl organic halo [ceyn [ceyn] freight method are disclosed to boron. (by machine translation)

Chemoselective coupling of 1,1-bis[(pinacolato)boryl]alkanes for the transition-metal-frec borylation of aryl and vinyl halides: A combined experimental and theoretical investigation

A new transition-metal-frec borylation of aryl and vinyl halides using l,l-bis[(pinacolato)boryl]alkanes as boron sources is described. In this transformation one of the boron groups from 1,1-bis[(pinacolato)boryl]alkanes is selectively transferred to aryl and vinyl halides in the presence of sodium tert-butoxide as the only activator to form organoboronate esters. Under the developed borylation conditions, a broad range of organohalides are borylated with excellent chemo-selectivity and functional group compatibility, thus offering a rare example of a transition-metal-frec borylation protocol. Experimental and theoretical studies have becn performed to elucidate the reaction mechanism, revealing the unusual formation of Lewis acid/base adduct betwecn organohalides and α-borylcarbanion, generated in situ from the reaction of l,l-bis[(pinacolato)boryl]alkanes with an alkoxide base, to facilitate the borylation reactions.

Cobalt-Catalyzed C(sp2)-H borylation with an air-stable, readily prepared terpyridine cobalt(II) Bis(acetate) precatalyst

A bench-stable, 4-aryl-substituted terpyridine supported, high-spin cobalt(II) bis(acetate) complex, (ArTpy)Co- (OAc)2 (ArTpy = 4′-(4-N,N′-dimethylaminophenyl)-2,2′:6′,2″- Terpyridine), is active for the C(sp2)-H borylation of arenes and heteroarenes with B2Pin2 (Pin = pinacolato). Optimization of the catalytic borylation reaction revealed improved performance in the presence of LiOMe and turnover numbers of up to 100 have been observed using all air-stable components. EPR specstroscopy identified formation of inactive cobalt species, promoted by excess HBPin. A high-spin cobalt(II) bis[(diacetoxy)- pinacolatoborate-κ3O,O,O] compound has been isolated and characterized by X-ray diffraction and is the result of catalyst deactivation.

Cobalt-Catalyzed Regioselective Borylation of Arenes: N-Heterocyclic Silylene as an Electron Donor in the Metal-Mediated Activation of C?H Bonds

C?H Borylation of arenes has been a subject of great interest recently because of its atom-economy and the wide applicability of borylated products in value-added synthesis. A new bis(silylene)cobalt(II) complex bearing a bis(N-heterocyclic silylene)-pyridine pincer ligand (SiNSi) has been synthesized and structurally characterized. It enabled the regioselective catalytic C?H borylation of pyridines, furans, and fluorinated arenes. Notably, it exhibited complementary regioselectivity for the borylation of fluorinated arenes compared to previously known catalytic systems, demonstrating that N-heterocyclic silylene donors have enormous potential in metal-catalyzed catalytic applications.

Preparing (Multi)Fluoroarenes as Building Blocks for Synthesis: Nickel-Catalyzed Borylation of Polyfluoroarenes via C-F Bond Cleavage

The [Ni(IMes)2]-catalyzed transformation of fluoroarenes into arylboronic acid pinacol esters via C-F bond activation and transmetalation with bis(pinacolato)diboron (B2pin2) is reported. Various partially fluorinated arenes with different degrees of fluorination were converted into their corresponding boronate esters.

Amine-borane complexes: Air- and moisture-stable partners for palladium-catalyzed borylation of aryl bromides and chlorides

A method for using amine-borane complexes directly in palladium catalyzed borylation has been developed. The reaction proceeds through the sequential formation of a boronium species followed by deprotonation leading to the aminoborane. This reagent is then directly used in the borylation process leading, after work-up, to various boronic acid derivatives. The reaction was applied to (hetero)aryl triflates, iodides, bromides and chlorides.

Fluorine-controlled C-H borylation of arenes catalyzed by a PSiN-pincer platinum complex

An efficient, regioselective synthesis of fluorine-substituted arylboronic esters was achieved through fluorine-controlled C-H borylation of arenes with diboron catalyzed by a PSiN-platinum complex. The promising utility of the PSiN-platinum catalyst and its unique regioselectivity were demonstrated for the first time, which would complement the well-developed Ir-catalyzed C-H borylation.

Single-crystal-to-single-crystal metalation of a metal-organic framework: A route toward structurally well-defined catalysts

Metal-organic frameworks featuring ligands with open chelating groups are versatile platforms for the preparation of a diverse set of heterogeneous catalysts through postsynthetic metalation. The crystalline nature of these materials allows them to be characterized via X-ray diffraction, which provides valuable insight into the structure of the metal sites that facilitate catalysis. A highly porous and thermally robust zirconium-based metal-organic framework, Zr6O4(OH)4(bpydc)6 (bpydc2- = 2,2′-bipyridne-5,5′-dicarboxylate), bears open bipyridine sites that readily react with a variety of solution- and gas-phase metal sources to form the corresponding metalated frameworks. Remarkably, Zr6O4(OH)4(bpydc)6 undergoes a single-crystal-to-single-crystal transformation upon metalation that involves a change in space group from Fm3m to Pa3. This structural transformation leads to an ordering of the metalated linkers within the framework, allowing structural characterization of the resulting metal complexes. Furthermore, Zr6O4(OH)4(bpydc)6 yields an active heterogeneous catalyst for arene C-H borylation when metalated with [Ir(COD)2]BF4 (COD = 1,5-cyclooctadiene). These results highlight the unique potential of metal-organic frameworks as a class of heterogeneous catalysts that allow unparalleled structural characterization and control over their active sites.

METHOD FOR PREPARING AMINOARYLBORANE COMPOUNDS OR DERIVATIVES THEREOF

The present invention provides a process for the preparation of aminoarylborane compounds and derivatives thereof comprising a step of arylation by reacting an aryl chloride with an aminoborane compound in the presence of a catalytic system.