288101-48-4

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1,5-DIFLUOROBENZENE is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with improved therapeutic properties.
Used in Agrochemical Production:
In the agrochemical industry, 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1,5-DIFLUOROBENZENE is utilized as a precursor for the production of agrochemicals. Its incorporation into these products can enhance their effectiveness in pest control and crop protection.
Used in Advanced Materials:
2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1,5-DIFLUOROBENZENE is employed as a building block in the development of advanced materials with specific properties. Its unique structure contributes to the creation of materials with improved performance characteristics.
Used in the Production of Boron-Containing Polymers:
As a precursor, 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1,5-DIFLUOROBENZENE is used in the synthesis of boron-containing polymers. These polymers have potential applications in various fields, including electronics, sensors, and energy storage.
Used as a Reagent in Organic Reactions:
In organic chemistry, 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1,5-DIFLUOROBENZENE serves as a reagent in various organic reactions. Its unique properties enable it to facilitate specific chemical transformations, contributing to the synthesis of complex organic molecules.

InChI:InChI=1/C12H15BF2O2/c1-11(2)12(3,4)17-13(16-11)9-6-5-8(14)7-10(9)15/h5-7H,1-4H3

Upstream product

• 348-57-2 2,4-difluorobromobenzene 
• 73183-34-3 bis(pinacol)diborane 
• 372-18-9 1,3-Difluorobenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 367-23-7 1,2,4-trifluorobenzene 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 1344146-05-9 dimethyl 6-(2,4-difluorophenyl)-2,2'-bipyridine-4,4'-dicarboxylate 
• 1344146-06-0 6-(2,4-difluorophenyl)-2,2'-bipyridine-4,4'-dicarboxylic acid 
• 931430-51-2 2-phenylvinylboronic acid 
• 837383-75-2 2-(2,4-difluorophenyl)benzo[d]thiazole 
• 512180-22-2 2-(2,4-difluorophenyl)-quinoline 
• 391604-55-0 2-(2,4-difluorophenyl)pyridine 
• 372-18-9 1,3-Difluorobenzene 
• 872545-53-4 2,4,4'-trifluoro-1,1'-biphenyl 
• 917495-77-3 2-(2',4'-difluorophenyl)-4-bromopyridine 

Relevant academic research and scientific papers

Direct C?H Borylation of Arenes Catalyzed by Saturated Hydride-Boryl-Iridium-POP Complexes: Kinetic Analysis of the Elemental Steps

The saturated trihydride IrH3{κ3-P,O,P-[xant(PiPr2)2]} (1; xant(PiPr2)2=9,9-dimethyl-4,5-bis(diisopropylphosphino)xanthene) activates the B?H bond of two molecules of pinacolborane (HBpin) to give H2, the hydride-boryl derivatives IrH2(Bpin){κ3-P,O,P-[xant(PiPr2)2]} (2) and IrH(Bpin)2{κ3-P,O,P-[xant(PiPr2)2]} (3) in a sequential manner. Complex 3 activates a C?H bond of two molecules of benzene to form PhBpin and regenerates 2 and 1, also in a sequential manner. Thus, complexes 1, 2, and 3 define two cycles for the catalytic direct C?H borylation of arenes with HBpin, which have dihydride 2 as a common intermediate. C?H bond activation of the arenes is the rate-determining step of both cycles, as the C?H oxidative addition to 3 is faster than to 2. The results from a kinetic study of the reactions of 1 and 2 with HBpin support a cooperative function of the hydride ligands in the B?H bond activation. The addition of the boron atom of the borane to a hydride facilitates the coordination of the B?H bond through the formation of κ1- and κ2-dihydrideborate intermediates.

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.

C-H borylation by platinum catalysis

Herein, we describe the platinum-catalyzed borylation of aromatic C-H bonds. N-Heterocyclic carbene-ligated platinum catalysts are found to be efficient catalysts for the borylation of aromatic C(sp2)-H bonds when bis(pinacolato)diboron is used as the boron source. The most remarkable feature of these Pt catalysts is their lack of sensitivity towards the degree of steric hindrance around the C-H bonds undergoing the borylation reaction. These Pt catalysts allow for the synthesis of sterically congested 2,6-disubstituted phenylboronic esters, which are otherwise difficult to synthesize using existing C-H borylation methods. Furthermore, platinum catalysis allows for the site-selective borylation of the C-H bonds ortho to fluorine substituents in fluoroarene systems. Preliminary mechanistic studies and work towards the synthetic application of this platinum catalyzed C-H borylation process are described.

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.

Miyaura Borylation and One-Pot Two-Step Homocoupling of Aryl Chlorides and Bromides under Solvent-Free Conditions

Solvent-free protocols for Miyaura borylation and the one-pot, two-step homocoupling of aryl halides are reported for the first time. Bis(dibenzylideneacetone)palladium(0) [Pd(dba)2] is an optimal source of palladium for Miyaura borylation, while for one-pot two-step homocoupling palladium(II) acetate [Pd(OAc)2] gives highest yields. Aryl bromides are coupled most efficiently using the DPEphos ligand. Chlorides are coupled using XPhos. The developed protocols are robust, versatile and easily reproducible on a large scale.

POP-rhodium-promoted C-H and B-H bond activation and C-B bond formation

The square-planar monohydride complex RhH{xant(PiPr2)2} (1; xant(PiPr2)2 = 9,9-dimethyl-4,5-bis(diisopropylphosphino)xanthene) activates C-H bonds of arenes. Heating of benzene solutions of 1 at 80 °C affords RhPh{xant(PiPr2)2} (2). Under the same conditions, toluene gives Rh(m-tolyl){xant(PiPr2)2} (3a) and Rh(p-tolyl){xant(PiPr2)2} (3b) in a 78:22 molar ratio, whereas m-xylene leads to Rh(C6H3-3,5-Me2){xant(PiPr2)2} (4). At room temperature, fluorobenzene and 1,3-difluorobenzene generate Rh(C6H4-2-F){xant(PiPr2)2} (5) and Rh(C6H3-2,6-F2){xant(PiPr2)2} (6), respectively. Complex 1 also promotes the B-H bond activation of pinacolborane (HBpin) and catecholborane (HBcat). The reactions initially give the trans-dihydride derivatives RhH2(BR2){xant(PiPr2)2} (BR2 = Bpin (7), Bcat (8)), which lose H2 to afford the square-planar Rh(BR2){xant(PiPr2)2} (BR2 = Bpin (9), Bcat (10)). Complex 2 reacts with HBpin to regenerate 1 and to give Ph-Bpin. Similarly, complex 9 regenerates 1 and gives Ph-Bpin by reaction with benzene. In agreement with these transformations, complex 1 catalyzes the direct C-H borylation of arenes. The selectivity of the process appears to be governed by the kinetic of the C-H bond activations of the arenes. Benzylic borylation is not observed for methylbenzenes. The first X-ray structure of a square-planar rhodium-boryl complex is also reported.

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.

Regioselective electrophilic borylation of haloarenes

Haloarenes undergo direct borylation using amine:BCl3:AlCl3 in the ratio of 1:1:2. After esterification the pinacol boronate esters are isolated in good yield with regioselectivity controlled by steric and electronic effects.

C-H Functionalization at Sterically Congested Positions by the Platinum-Catalyzed Borylation of Arenes

Despite significant progress in the area of C-H bond functionalization of arenes, no general method has been reported for the functionalization of C-H bonds at the sterically encumbered positions of simple arenes, such as mesitylene. Herein, we report the development of the first platinum-based catalyst for C-H borylation of arenes and heteroarenes. Notably, this method exhibited high tolerance toward steric hindrance and provided rapid access to a series of 2,6-disubstituted phenylboronic esters, valuable building blocks for further elaborations.

Transition metal-free synthesis of pinacol arylboronate: Regioselective boronation of 1,3-disubstituted benzenes

The regioselective synthesis of pinacol arylboronate has been achieved from 1,3-disubstituted benzene through directed ortho-metallation (DoM)-borylation sequence. A wide range of substituents and borylating reagents were investigated. In situ lithiation and subsequent boronation predominantly occurred at the ortho-position to afford the desired products in moderate yields. CSIRO 2014.