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Usage

Uses

Used in Organic Synthesis:
3,5-Bis(trifluoroMethyl)phenylboronic acid pinacol ester is used as a reagent in organic synthesis for the formation of carbon-carbon and carbon-heteroatom bonds. Its unique structure allows for the creation of diverse molecular architectures, making it a valuable tool in the synthesis of complex organic molecules.
Used in the Suzuki-Miyaura Coupling Reaction:
In the field of organic chemistry, 3,5-Bis(trifluoroMethyl)phenylboronic acid pinacol ester is used as a key component in the Suzuki-Miyaura coupling reaction. This widely-used method facilitates the formation of biaryl compounds, which are important structural motifs in various pharmaceuticals, agrochemicals, and materials.
Used in Drug Discovery:
3,5-Bis(trifluoroMethyl)phenylboronic acid pinacol ester is employed in drug discovery as a building block for the synthesis of bioactive molecules. Its ability to form diverse molecular structures makes it a promising candidate for the development of new drugs with potential therapeutic applications.
Used in Material Science:
In the realm of material science, 3,5-Bis(trifluoroMethyl)phenylboronic acid pinacol ester is utilized in the synthesis of novel materials with unique properties. Its versatility in forming carbon-carbon and carbon-heteroatom bonds contributes to the development of advanced materials for various applications, such as electronics, optoelectronics, and nanotechnology.

Upstream product

• 188290-36-0 thiophene 
• 73183-34-3 bis(pinacol)diborane 
• 328-74-5 3,5-Bis-(trifluoromethyl)aniline 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 73852-19-4 3,5-bis-trifluromethylphenylboronic acid 
• 328-70-1 3,6-bis(trifluoromethyl)bromobenzene 
• 130783-02-7 3,5-bis(trifluoromethyl)thiophenol 
• 328-72-3 3,5-(bistrifluoromethyl)chlorobenzene 
• 785-56-8 3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride 
• 1435466-10-6 S-ethyl 3,5-bis(trifluoromethyl)benzenecarbothioate 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 22092-92-8 diisopropopylaminoborane 
• 73852-85-4 3,5-bis(trifluoromethyl)phenylboronic acid pyrocatechol ester 
• 402-31-3 1,3-bis(trifluoromethyl)benzene 

Downstream Products

• 328-70-1 3,6-bis(trifluoromethyl)bromobenzene 
• 1442416-49-0 C₁₉H₁₈F₆ 
• 1352918-79-6 C₁₆H₁₂F₆ 
• 1380226-51-6 N,N-dibenzyl-3,5-bis(trifluoromethyl)aniline 
• 1313373-83-9 9,10-bis(3,5-bis(trifluoromethyl)phenyl)-2,3,6,7-tetrakis(4-tertbutylphenyl)anthracene 
• 1258071-62-3 4-(3,5-bis(trifluoromethyl)phenyl)butan-2-one 
• 1258071-63-4 3-(3,5-bis(trifluoromethyl)phenyl)cyclohexanone 
• 1224867-31-5 C₂₄H₂₂F₆N₂SSi 
• 1224867-25-7 C₂₂H₂₀F₆O₂S₂Si 
• 73852-19-4 3,5-bis-trifluromethylphenylboronic acid 
• 729-81-7 1,3,5-tris(trifluoromethyl)benzene 
• 42450-72-6 (3,5-bistrifluoromethylphenyl)(methyl)amine 

Relevant academic research and scientific papers

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

Sequential Ir/Cu-Mediated Method for the Meta-Selective C-H Radiofluorination of (Hetero)Arenes

This article describes a sequential Ir/Cu-mediated process for the meta-selective C-H radiofluorination of (hetero)arene substrates. In the first step, Ir-catalyzed C(sp2)-H borylation affords (hetero)aryl pinacolboronate (BPin) esters. The intermediate organoboronates are then directly subjected to copper-mediated radiofluorination with [18F]tetrabutylammonium fluoride to afford fluorine-18 labeled (hetero)arenes in high radiochemical yield and radiochemical purity. This entire process is performed on a benchtop without Schlenk or glovebox techniques and circumvents the need to isolate (hetero)aryl boronate esters. The reaction was automated on a TracerLab FXFN module with 1,3-dimethoxybenzene and a meta-tyrosine derivative. The products, [18F]1-fluoro-3,5-dimethoxybenzene and an 18F-labeled meta-tyrosine derivative, were obtained in 37 ± 5% isolated radiochemical yield and >99% radiochemical purity and 25% isolated radiochemical yield and 99% radiochemical purity, and 0.52 Ci/μmol (19.24 GBq/μmol) molar activity (Am), respectively.

Cross-Coupling through Ag(I)/Ag(III) Redox Manifold

In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e? redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: i) easy AgI/AgIII 2e? oxidation mediated by air; ii) bpy/phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]? (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]? intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.

Organic compound and electroluminescent device using same

The present invention provides an organic compound and an electroluminescent device using the same. The organic compound has a structure represented by a formula I, and the organic compound provided by the present invention is a D-carbazole-A configuratio

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.

Facile and economical Miyaura borylation and one-pot Suzuki–Miyaura cross-coupling reaction

Facile and economical method for Miyaura borylation reaction between B2pin2 and aryl bromides is reported. The catalytic system containing 2 mol% PdCl2(PPh3)2 and KOAc serves to enable borylations to occur under solvent-free and atmospheric conditions. The developed protocol can be applied to synthesize symmetrical and unsymmetrical biaryls via one-pot two-step Suzuki–Miyaura cross-coupling reaction and also offers the up-scalability.

Highly Selective and Divergent Acyl and Aryl Cross-Couplings of Amides via Ir-Catalyzed C-H Borylation/N-C(O) Activation

Herein, we demonstrate that amides can be readily coupled with nonactivated arenes via sequential Ir-catalyzed C-H borylation/N-C(O) activation. This methodology provides facile access to biaryl ketones and biaryls by the sterically controlled Ir-catalyzed C-H borylation and divergent acyl and decarbonylative amide N-C(O) and C-C activation. The methodology diverts the traditional acylation and arylation regioselectivity, allowing us to directly utilize readily available arenes and amides to produce valuable ketone and biaryl motifs.

Copper-catalysed borylation of aryl chlorides

We report herein the first Cu-catalysed borylation of a wide range of aryl chlorides with different electronic and steric properties using a readily prepared NHC-stabilised Cu catalyst and KOtBu as the base with B2pin2 (pin = pinacolato) as the boron reagent. The aryl chlorides are converted into their corresponding arylboronic esters in good yields. The new procedure shows broad functional group tolerance, and B2neop2 (neop = neopentyl glycolato) can also be applied as the boron reagent.

Pluripotent Features of Doubly Thiophene-Fused Benzodiphospholes as Organic Functional Materials

Linear ladder-type π-conjugated molecules have attracted much interest because of their intriguing physicochemical properties. To modulate their electronic structures, an effective strategy is to incorporate main-group elements into ladder-type π-conjugated molecules. In line with this strategy, a variety of ladder-type π-conjugated molecules with main-group elements have been synthesized to explore their potential utility as organic functional materials. In this context, phosphole-based π-conjugated molecules are highly attractive, owing to their unique optical and electrochemical properties, which arise from the phosphorus atom. Herein, the synthesis and physicochemical properties of doubly thiophene-fused benzodiphospholes, as a new class of phosphole-based ladder-type π-conjugated molecule, are reported. Systematic investigations into the physicochemical properties of doubly thiophene-fused benzodiphospholes revealed their pluripotent features: intense near-infrared fluorescence, excellent two-photon absorption property, and remarkably high electron-transporting ability. This study demonstrates the potential utility of doubly thiophene-fused benzodiphospholes as organic functional materials for biological imaging, nonlinear optics, organic transistors, and organic photovoltaics.

Energy level tuning of ‘Z'-shaped small molecular non-fullerene electron acceptors based on a dipyrrolo[2,3-b:2′,3′-e]pyrazine-2,6(1H,5H)-dione acceptor unit for organic photovoltaic applications: a joint experimental and DFT investigation on the effect o

Three different fluorine (4-CF3, 3,5-CF3 and 3,4,5-F) end-capped, A2-π-A1-π-A2 type small molecular non-fullerene acceptor molecules (1CFPzDP, 2CFPzDP, and 3FPzDP) containing a common central core acc