214360-65-3

Usage

Uses

Used in Organic Synthesis:
4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER is used as a reagent for the formation of carbon-carbon and carbon-heteroatom bonds, which are crucial in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER is used as a key intermediate in the synthesis of various drugs. Its ability to form new bonds makes it valuable for the development of novel pharmaceutical compounds with specific therapeutic properties.
Used in Agrochemical Industry:
4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER is utilized as a building block in the creation of agrochemicals, contributing to the development of new pesticides and other agricultural chemicals that can improve crop protection and yield.
Used in Materials Science:
In the field of materials science, 4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER is employed in the synthesis of advanced materials with unique properties, such as high-performance polymers and specialty materials for various applications.
Used in Suzuki-Miyaura Cross-Coupling Reaction:
4-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER is used as a nucleophile in the Suzuki-Miyaura cross-coupling reaction, a widely employed method for the formation of new carbon-carbon bonds, which is essential for the synthesis of a broad range of organic compounds, including those with potential applications in medicine, materials, and other industries.

InChI:InChI=1/C14H16BF3O3/c1-13(2)14(3,4)21-15(20-13)9-5-7-10(8-6-9)19-12(18)11(16)17/h5-8H,1-4H3

Upstream product

• 98-08-8 α,α,α-trifluorotoluene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 51901-85-0 bromocatecholborane 
• 7440-66-6 zinc 
• 98-56-6 4-chlorobenzotrifluoride 
• 455-14-1 4-trifluoromethylphenylamine 
• 73183-34-3 bis(pinacol)diborane 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 69180-48-9 (4-(trifluoromethyl)phenyl)-λ³-iodanediyl diacetate 
• 871362-15-1 bis(4-(trifluoromethyl)phenyl)iodonium trifluoromethanesulfonate 
• 455-13-0 4-Iodobenzotrifluoride 
• 22092-92-8 diisopropopylaminoborane 

Downstream Products

• 1008756-39-5 C₂₀H₁₂F₆S 
• 1187791-58-7 2-(4-trifluoromethylphenyl)cyclopent-2-enone 
• 1234215-27-0 1-(hex-1-en-3-yl)-4-(trifluoromethyl)benzene 
• 1373773-66-0 2,5-bis(3’-hexyl-5’-[4-(trifluoromethyl)phenyl]thiophen-2’-yl)thiazolo-[5,4-d]thiazole 
• 402-44-8 4-Fluorobenzotrifluoride 
• 128814-90-4 2-(4-(trifluoromethyl)phenyl)-4H-chromen-4-one 

Relevant academic research and scientific papers

Conclusive Evidence on the Mechanism of the Rhodium-Mediated Decyanative Borylation

The stoichiometric reactions proposed in the mechanism of the rhodium-mediated decyanative borylation have been performed and all relevant intermediates isolated and characterized including their X-ray structures. Complex RhCl{xant(PiPr2)2} (1, xant(PiPr2)2 = 9,9-dimethyl-4,5-bis(diisopropylphosphino)xanthene) reacts with bis(pinacolato)diboron (B2pin2), in benzene, to give the rhodium(III) derivative RhHCl(Bpin){xant(PiPr2)2} (4) and PhBpin. The reaction involves the oxidative addition of B2pin2 to 1 to give RhCl(Bpin)2{xant(PiPr2)2}, which eliminates ClBpin generating Rh(Bpin){xant(PiPr2)2} (2). The reaction of the latter with the solvent yields PhBpin and the monohydride RhH{xant(PiPr2)2} (6), which adds the eliminated ClBpin. Complex 4 and its catecholboryl counterpart RhHCl(Bcat){xant(PiPr2)2} (7) have also been obtained by oxidative addition of HBR2 to 1. Complex 2 is the promoter of the decyanative borylation. Thus, benzonitrile and 4-(trifluoromethyl)benzonitrile insert into the Rh-B bond of 2 to form Rh{C(R-C6H4)-NBpin}{xant(PiPr2)2} (R = H (8), p-CF3 (9)), which evolve into the aryl derivatives RhPh{xant(PiPr2)2} (3) and Rh(p-CF3-C6H4){xant(PiPr2)2} (10), as a result of the extrusion of CNBpin. The reactions of 3 and 10 with B2pin2 yield the arylBpin products and regenerate 2.

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

Unreactive C-N Bond Activation of Anilines via Photoinduced Aerobic Borylation

Unreactive C-N bond activation of anilines was achieved by photoinduced aerobic borylation. A diverse range of tertiary and secondary anilines were converted to aryl boronate esters in moderate to good yields with wide functional group tolerance under simple and ambient photochemical conditions. This transformation achieved the direct and facile C-N bond activation of unreactive anilines, providing a convenient and practical route transforming widely available anilines into useful aryl boronate esters.

Palladium-catalyzed borylation of aryl bromides and chlorides using phosphatrioxa-adamantane ligands

Catalysts based on the combination of Pd(OAc)2 and the electron-deficient phosphatrioxa-adamantane ligands are described for borylation of aryl bromides and chlorides. Catalytic evaluation of a small library of phosphatrioxa-adamantane ligands provided some insights on the preferred ligand steric profile for borylation reactions. The corresponding aryl boronate esters were accessed under mild conditions (25–70 °C) and isolated in high yields (up to 96%).

Photochemical and electrochemical C-N borylation of arylhydrazines

The C-N borylation of arylhydrazine hydrochlorides with bis(pinacolato)diboron was achieved under photochemical and electrochemical conditions, respectively. This novel and scalable transformation provides two efficient and mild transition-metal-free synt

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.

Recyclable Pd2dba3/XPhos/PEG-2000 System for Efficient Borylation of Aryl Chlorides: Practical Access to Aryl Boronates

Pd2dba3/XPhos in poly(ethylene glycol) (PEG-2000) is shown to be a highly stable and efficient catalyst for the borylation of aryl chlorides with bis(pinacolato)diboron. The borylation reaction proceeds smoothly at 110 °C, delivering a wide variety of aryl boronates in good to excellent yields with high functional group tolerance. The crude products were easily isolated via simple extraction of the reaction mixture with cyclohexane. Moreover, both expensive Pd2dba3 and XPhos in PEG-2000 system could be readily recycled and reused more than six times without loss of catalytic efficiency.

Unveiling Extreme Photoreduction Potentials of Donor-Acceptor Cyanoarenes to Access Aryl Radicals from Aryl Chlorides

Since the seminal work of Zhang in 2016, donor-acceptor cyanoarene-based fluorophores, such as 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN), have been widely applied in photoredox catalysis and used as excellent metal-free alternatives to noble metal Ir- and Ru-based photocatalysts. However, all the reported photoredox reactions involving this chromophore family are based on harnessing the energy from a single visible light photon, with a limited range of redox potentials from -1.92 to +1.79 V vs SCE. Here, we document the unprecedented discovery that this family of fluorophores can undergo consecutive photoinduced electron transfer (ConPET) to achieve very high reduction potentials. One of the newly synthesized catalysts, 2,4,5-tri(9H-carbazol-9-yl)-6-(ethyl(phenyl)amino)isophthalonitrile (3CzEPAIPN), possesses a long-lived (12.95 ns) excited radical anion form, 3CzEPAIPN?-*, which can be used to activate reductively recalcitrant aryl chlorides (Ered ≈ -1.9 to -2.9 V vs SCE) under mild conditions. The resultant aryl radicals can be engaged in synthetically valuable aromatic C-B, C-P, and C-C bond formation to furnish arylboronates, arylphosphonium salts, arylphosphonates, and spirocyclic cyclohexadienes.

Ligand-Enabled, Iridium-Catalyzed ortho-Borylation of Fluoroarenes

A terpyridine derivative and an iridium complex catalyze the C-H borylation of a stoichiometric amount of a fluoroarene with high ortho-selectivity and tolerance of functional groups such as bromide, chloride, ester, ketone, amine, and in situ-borylated hydroxyl. Complex drug molecules such as haloperidol can be selectively borylated ortho to the F atom. The terpyridine ligand undergoes rollover cyclometalation to produce an N,N,C-coordinated iridium complex, which may either selectively borylate the fluoroarene by itself or undergo reductive elimination to produce a borylated ligand.

Carbon-carbon bond activation by B(OMe)3/B2pin2-mediated fragmentation borylation

Selective carbon-carbon bond activation is important in chemical industry and fundamental organic synthesis, but remains challenging. In this study, non-polar unstrained Csp2-Csp3 and Csp2-Csp2 bond activation was achieved by B(OMe)3/B2pin2-mediated fragmentation borylation. Various indole derivatives underwent C2-regioselective C-C bond activation to afford two C-B bonds under transition-metal-free conditions. Preliminary mechanistic investigations suggested that C-B bond formation and C-C bond cleavage probably occurred in a concerted process. This new reaction mode will stimulate the development of reactions based on inert C-C bond activation. This journal is