87100-28-5

Usage

Uses

Used in Pharmaceutical Industry:
Benzylboronic acid pinacol ester is used as a synthetic intermediate for the preparation of pharmaceutical compounds. Its ability to undergo palladium-catalyzed coupling reactions enables the formation of complex organic molecules, which are often found in drug candidates and active pharmaceutical ingredients.
Used in Organic Synthesis:
In the field of organic synthesis, benzylboronic acid pinacol ester is used as a reagent for the construction of various organic molecules. Its participation in palladium-catalyzed coupling reactions allows for the formation of carbon-carbon and carbon-heteroatom bonds, which are essential for the synthesis of a wide range of organic compounds.
Used in Pd (0)-mediated [11C] Carbonylation Reaction:
Benzylboronic acid pinacol ester finds application in Pd (0)-mediated [11C] carbonylation reactions, which are important for the synthesis of radiolabeled compounds used in positron emission tomography (PET) imaging. This application takes advantage of the reactivity of the boronic acid moiety in the presence of palladium catalysts, allowing for the incorporation of the radioactive carbon-11 isotope into the target molecule.

InChI:InChI=1/C13H19BO2/c1-12(2)13(3,4)16-14(15-12)10-11-8-6-5-7-9-11/h5-9H,10H2,1-4H3

Upstream product

• 108-88-3 toluene 
• 73183-34-3 bis(pinacol)diborane 
• 100-39-0 benzyl bromide 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 100-44-7 benzyl chloride 
• 1024-41-5 benzyl tosylate 
• 55791-06-5 benzyl mesylate 
• 100-51-6 benzyl alcohol 
• 745783-97-5 triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 100-46-9 benzylamine 
• 17763-67-6 Phenyl triflate 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 129422-12-4 ((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)zinc(II) iodide 

Downstream Products

• 1253573-80-6 4-(5-benzyl-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine 
• 42116-44-9 N-tert-butoxycarbonylbenzylamine 
• 109774-57-4 N,N-bis(tert-butoxycarbonyl)benzylamine 
• 100-46-9 benzylamine 
• 100-41-4 ethylbenzene 
• 57693-15-9 2-benzyl-3-chloropyrazine 
• 23096-47-1 1-(4-fluorophenyl)-2-phenylethan-1-ol 
• 5422-47-9 1-(4-methoxyphenyl)-2-phenylethan-1-ol 
• 136757-49-8 2-phenyl-1-(4-(trifluoromethyl)phenyl)ethan-1-ol 
• 20498-65-1 1--2-phenyl-aethanol 
• 22817-11-4 1-(2-methylphenyl)-2-phenylethanol 
• 31233-60-0 1-[4-(dimethylamino)phenyl]-2-phenylethanol 
• 79419-76-4 3-benzyl-3-hydroxy-1-methyl-1,3-dihydroindol-2-one 
• 5342-87-0 1,2-diphenylpropane-2-ol 

Relevant academic research and scientific papers

Selective Benzylic CH-Borylations by Tandem Cobalt Catalysis

Metal-catalyzed C?H activations are environmentally and economically attractive synthetic strategies for the construction of functional molecules as they obviate the need for pre-functionalized substrates and minimize waste generation. Great challenges reside in the control of selectivities, the utilization of unbiased hydrocarbons, and the operation of atom-economical dehydrocoupling mechanisms. An especially mild borylation of benzylic CH bonds was developed with the ligand-free pre-catalyst Co[N(SiMe3)2]2 and the bench-stable and inexpensive borylation reagent B2pin2 that produces H2 as the only by-product. A full set of kinetic, spectroscopic, and preparative mechanistic studies are indicative of a tandem catalysis mechanism of CH-borylation and dehydrocoupling via molecular CoI catalysts.

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

C(sp3)-H selective benzylic borylation by in situ reduced ultrasmall Ni species on CeO2

Herein, we report that highly dispersed Ni hydroxide species supported on CeO2 act as an efficient heterogeneous catalyst for the selective borylation of benzylic C(sp3)-H bonds of alkylarenes including secondary derivatives, using pinacolborane as the bo

Boronic acid derivatives

The present invention relates to boronic acid derivatives; the present invention provides compounds of formula (I) or pharmaceutically acceptable salts, solvates, polymorphs or isomers thereof, pharmaceutical compositions comprising these compounds, and u

Boronic acid derivatives

The present invention relates to boronic acid derivatives; the present invention provides compounds of formula (I) or pharmaceutically acceptable salts, solvates, polymorphs or isomers thereof, pharmaceutical compositions comprising these compounds, and uses of such compounds in the treatment of lmp7-related diseases.

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.

Visible-light-driven graphene supported Cu/Pd alloy nanoparticle-catalyzed borylation of alkyl bromides and chlorides in air

A highly efficient photocatalytic protocol for borylation of alkyl bromides and chlorides with graphene supported Cu/Pd alloy nanoparticles as a heterogeneous catalyst is reported. This photocatalytic system operates with visible light in air, providing a wide range of primary and secondary alkyl halides with B2pin2 or B2neop2 in high yields at low temperatures, thereby demonstrating its broad utility and functional group tolerance. The high performance is attributed to a synergistic effect of localized surface plasmon resonance (LSPR) of Cu and charge transfer from Cu to Pd due to the alloy surface charge heterogeneity. Transfer of energetic electrons from Pd to electrophilic alkyl halides lead to the formation of the alkyl radicals, which quickly react with a nucleophilic adduct of a diboron compound with base adsorbed on the positively charged Cu sites to form the corresponding borylation product.

Photochemical Radical C–H Halogenation of Benzyl N-Methyliminodiacetyl (MIDA) Boronates: Synthesis of α-Functionalized Alkyl Boronates

α-Haloboronates are useful organic synthons that can be converted to a diverse array of α-substituted alkyl borons. Methods to α-haloboronates are limiting and often suffer from harsh reaction conditions. Reported herein is a photochemical radical C-H halogenation of benzyl N-methyliminodiacetyl (MIDA) boronates. Fluorination, chlorination, and bromination reactions were effective by using this protocol. Upon reaction with different nucleophiles, the C?Br bond in the brominated product could be readily transformed to a series of C?C, C?O, C?N, C?S, C?P, and C?I bonds, some of which are difficult to forge with α-halo sp2-B boronate esters. An activation effect of B(MIDA) moiety was found.

Structure-Based Optimization and Discovery of M3258, a Specific Inhibitor of the Immunoproteasome Subunit LMP7 (β5i)

Proteasomes are broadly expressed key components of the ubiquitin-dependent protein degradation pathway containing catalytically active subunits (β1, β2, and β5). LMP7 (β5i) is a subunit of the immunoproteasome, an inducible isoform that is predominantly expressed in hematopoietic cells. Clinically effective pan-proteasome inhibitors for the treatment of multiple myeloma (MM) nonselectively target LMP7 and other subunits of the constitutive proteasome and immunoproteasome with comparable potency, which can limit the therapeutic applicability of these drugs. Here, we describe the discovery and structure-based hit optimization of novel amido boronic acids, which selectively inhibit LMP7 while sparing all other subunits. The exploitation of structural differences between the proteasome subunits culminated in the identification of the highly potent, exquisitely selective, and orally available LMP7 inhibitor 50 (M3258). Based on the strong antitumor activity observed with M3258 in MM models and a favorable preclinical data package, a phase I clinical trial was initiated in relapsed/refractory MM patients.

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.