253342-48-2

Usage

Uses

suzuki reaction

InChI:InChI=1/C13H19BO2/c1-10-7-6-8-11(9-10)14-15-12(2,3)13(4,5)16-14/h6-9H,1-5H3

Upstream product

• 108-88-3 toluene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 195062-57-8 p-tolylboronic pinacol ester 
• 195062-59-0 2-methylphenylboronic acid pinacol ester 
• 62-53-3 aniline 
• 502630-89-9 2-(3-chloro-5-methylphenyl)-4,4,5,5-tetra methyl-1,3,2-dioxaborolane 
• 745783-97-5 triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 17933-03-8 m-tolylboronic acid 
• 28987-79-3 m-tolylmagnesium bromide 
• 591-17-3 meta-bromotoluene 
• 185990-03-8 dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 108-44-1 1-amino-3-methylbenzene 

Downstream Products

• 17933-03-8 m-tolylboronic acid 
• 612-75-9 3,3'-dimethyl-biphenyl 
• 1256781-59-5 2-(2-bromo-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 76650-29-8 4-acetyl-3'-methylbiphenyl 
• 401-79-6 1-methyl-3-trifluoromethyl-benzene 
• 1583286-11-6 3-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)-5-methylphenol 
• 942069-53-6 2-(3-bromo-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 124289-21-0 3-bromo-5-methylbenzonitrile 
• 1073339-01-1 2-(3-iodo-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1369782-73-9 C₈H₆F₃I 
• 1583285-83-9 C₂₀H₃₉BO₄Si₃ 
• 643-65-2 3-methyl benzophenone 
• 108-39-4 3-methyl-phenol 
• 15286-13-2 diethyl (m-tolyl)phosphonate 

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

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%).

Mono-Phosphine Metal-Organic Framework-Supported Cobalt Catalyst for Efficient Borylation Reactions

We report a metal-organic framework (MOF) supported monoligated phosphine-cobalt complex, which is an active heterogeneous catalyst for aromatic C?H borylation and alkene hydroboration. The mono(phosphine)-Co catalyst (MOF?P?Co) was prepared by metalation of a porous triarylphosphine-functionalized MOF (MOF?P) with CoCl2 followed by activation with NaEt3BH. The MOF catalyst has a broad substrate scope with excellent functional group tolerance to afford arene- and alkyl-boronate esters in excellent yields and selectivity. MOF?P?Co gave a turnover number (TON) of 30,000 and could be recycled and reused at least 13 times in arene C?H borylation. Importantly, the attempt to prepare the homogeneous control (Ph3P?Co) using triphenylphosphine was unsuccessful due to the facile disproportionation reactions or intermolecular ligand exchanges in the solution. In contrast, the site isolation of the active mono(phosphine)-Co species within the MOF affords the robust and coordinatively unsaturated metal complexes, allowing to explore their catalytic properties and the reaction mechanism.

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

Remote steric control for undirected meta-selective C-H activation of arenes

Regioselective functionalization of arenes remains a challenging problem in organic synthesis. Steric interactions are often used to block sites adjacent to a given substituent, but they do not distinguish the remaining remote sites. We report a strategy

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.

The functionalization of benzene by boranes using trispyrazolylborate complexes

The catalytic C[sbnd]H activation and borylation of arenes by trispyrazolylborate complexes is reported. Trispyrazolylborate rhodium and iridium complexes have been previously shown to activate a variety of C[sbnd]H bonds. Here, we show the catalytic borylation of arenes by the trispyrazolylborate ethylene complexes Tp'Rh(C2H4)2, and Tp'Ir(C2H4)2.

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.

Method for catalytically synthesizing phenylboronic acid ester derivative by iridium catalyst

The invention relates to a method for catalytically synthesizing a phenylboronic acid ester derivative by using an iridium catalyst. The method comprises the following steps: by using a cyclooctadieneiridium chloride dimer as a catalyst, dissolving aryl halide and pinacol borane in an organic solvent to react, and carrying out aftertreatment to obtain the phenylboronic acid ester derivative. Compared with the prior art, the method has the advantages that the method is simple and green, cheap, readily available and stable raw materials of aryl halide and pinacol borane are used, the reaction conditions are mild, corresponding products can be obtained at high yield through reaction at room temperature in a non-inert atmosphere, and the method has good substrate universality, so that the method is better convenient to apply.

Catalytic Boration of Alkyl Halides with Borane without Hydrodehalogenation Enabled by Titanium Catalyst

An unprecedented and general titanium-catalyzed boration of alkyl (pseudo)halides (alkyl-X, X=I, Br, Cl, OMs) with borane (HBpin, HBcat) is reported. The use of titanium catalyst can successfully suppress the undesired hydrodehalogenation products that prevail using other transition-metal catalysts. A series of synthetically useful alkyl boronate esters are readily obtained from various (primary, secondary, and tertiary) alkyl electrophiles, including unactivated alkyl chlorides, with tolerance of other reducing functional groups such as ester, alkene, and carbamate. Preliminary studies on the mechanism revealed a possible radical reaction pathway. Further extension of our strategy to aryl bromides is also demonstrated.