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Usage

Uses

Used in Pharmaceutical Synthesis:
4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)FLUOROBENZENE is used as a key intermediate in the synthesis of complex organic molecules, particularly in the pharmaceutical industry. Its unique structure allows for the creation of a wide range of compounds with potential therapeutic applications.
Used in Organic Chemistry Research:
In the field of organic chemistry, 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)FLUOROBENZENE is used as a research compound for studying the properties and reactivity of organoboron compounds. Its involvement in chemical reactions, such as Suzuki coupling, makes it an important tool for understanding and developing new synthetic pathways.
Used in Material Science:
4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)FLUOROBENZENE is also used in material science as a component in the development of new materials with specific properties. Its ability to participate in various chemical reactions allows for the creation of materials with tailored characteristics for use in different applications.

InChI:InChI=1/C12H16BFO2/c1-11(2)12(3,4)16-13(15-11)9-5-7-10(14)8-6-9/h5-8H,1-4H3

Upstream product

• 352-33-0 1-Chloro-4-fluorobenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1765-93-1 4-fluoroboronic acid 
• 352-34-1 4-fluoro-1-iodobenzene 
• 73183-34-3 bis(pinacol)diborane 
• 462-06-6 fluorobenzene 
• 371-15-3 p-fluorothioanisole 
• 2714-90-1 phenyl 4-fluorobenzoate 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 540-36-3 para-difluorobenzene 
• 352-32-9 p-fluorotoluene 
• 824-80-6 sodium 4-fluorobenzenesulfinate 
• 349-88-2 4-Fluorobenzenesulfonyl chloride 

Downstream Products

• 99770-93-1 benzene-1,4-diboronic acid bispinacol ester 
• 352-32-9 p-fluorotoluene 
• 1187951-65-0 C₂₃H₁₈FN₃O₂S 
• 1187951-69-4 C₂₄H₂₀FN₃O₂S 
• 1233731-18-4 5-(4-fluorophenyl)-1-phenyl-1H-tetrazole 
• 324-74-3 4-fluoro-biphenyl 
• 1351476-56-6 C₂₅H₂₅FN₄ 
• 1351477-61-6 C₃₂H₃₁FN₄O₂S 
• 398-24-3 4-fluoro-4'-nitro-1,1'-biphenyl 
• 540-36-3 para-difluorobenzene 
• 1440511-71-6 7-(4-fluorophenyl)-4-methyl-1,2-dihydroquinolin-2-one 
• 180606-14-8 2-fluoro-6-(4-fluorophenyl)pyridine 
• 345-83-5 4-fluorobenzophenone 
• 1629-26-1 2-(4-fluorophenyl)-benzothiazole 

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

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

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.

Evaluation of the role of graphene-based Cu(i) catalysts in borylation reactions

Carbon-supported catalysts have been considered as macromolecular ligands which modulate the activity of the metallic catalytic center. Understanding the properties and the factors that control the interactions between the metal and support allows a fine tuning of the catalyzed processes. Although huge effort has been devoted to comprehending binding energies and charge transfer for single atom noble metals, the interaction of graphenic surfaces with cheap and versatile Cu(i) salts has been scarcely studied. A methodical experimental and theoretical analysis of different carbon-based Cu(i) materials in the context of the development of an efficient, general, scalable, and sustainable borylation reaction of aliphatic and aromatic halides has been performed. We have also examined the effect of microwave (MW) radiation in the preparation of these type of materials using sustainable graphite nanoplatelets (GNP) as a support. A detailed analysis of all the possible species in solution revealed that the catalysis is mainly due to an interesting synergetic Cu2O/graphene performance, which has been corroborated by an extensive theoretical study. We demonstrated through DFT calculations at a high level of theory that graphene enhances the reactivity of the metal in Cu2O against the halide derivative favoring a radical departure from the halogen. Moreover, this material is able to stabilize radical intermediates providing unexpected pathways not observed using homogeneous Cu(i) catalysed reactions. Finally, we proved that other common carbon-based supports like carbon black, graphene oxide and reduced graphene oxide provided poorer results in the borylation process.

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.

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

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.

Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation

Substantial effort is currently being devoted to obtaining photoredox catalysts with high redox power. Yet, it remains challenging to apply the currently established methods to the activation of bonds with high bond dissociation energy and to substrates with high reduction potentials. Herein, we introduce a novel photocatalytic strategy for the activation of inert substituted arenes for aryl borylation by using thiolate as a catalyst. This catalytic system exhibits strong reducing ability and engages non-activated Caryl–F, Caryl–X, Caryl–O, Caryl–N, and Caryl–S bonds in productive radical borylation reactions, thus expanding the available aryl radical precursor scope. Despite its high reducing power, the method has a broad substrate scope and good functional-group tolerance. Spectroscopic investigations and control experiments suggest the formation of a charge-transfer complex as the key step to activate the substrates.