401797-04-4

Usage

Uses

Used in Organic Synthesis:
3-Bromo-5-Methoxyphenylboronic Acid Pinacol Ester is used as a key intermediate in Suzuki-Miyaura coupling reactions, which are essential for forming carbon-carbon bonds. This application is crucial for constructing more complex chemical structures in various organic synthesis processes.
Used in Medicinal Chemistry:
In the pharmaceutical industry, 3-Bromo-5-Methoxyphenylboronic Acid Pinacol Ester serves as a valuable building block for the development of new drugs. Its unique chemical structure, including the boronic ester group and the bromine and methoxy substituents, allows for the creation of diverse and bioactive molecules with potential therapeutic applications.
Used in Chemical Research:
3-Bromo-5-Methoxyphenylboronic Acid Pinacol Ester is employed as a research tool in chemical laboratories to study the properties and reactivity of organoboron compounds. Its presence in various chemical reactions can provide insights into the mechanisms and selectivity of these processes, contributing to the advancement of chemical knowledge and techniques.

Upstream product

• 2398-37-0 3-methoxyphenyl bromide 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 27825-39-4 Robustoltrimethylaether 
• 27825-37-2 robustol 
• 1442416-20-7 C₁₁H₁₅BrO 
• 1442416-11-6 C₁₆H₁₇BrO 
• 1395093-30-7 2,2'-(oxybis([1,1'-biphenyl]-5,3-diyl))bis(1-(2,6-diisopropylphenyl)-1H-imidazole) 
• 1395093-29-4 5-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)-[1,1'-biphenyl]-3-ol 
• 1395093-28-3 1-(2,6-diisopropylphenyl)-2-(5-methoxy-[1,1'-biphenyl]-3-yl)-1H-imidazole 
• 1404169-12-5 N-(2,6-diisopropylphenyl)-5-methoxy-[1,1'-biphenyl]-3-carboximidamide 
• 867366-91-4 3-bromo-5-methoxybenzonitrile 

Relevant academic research and scientific papers

NNB-type tridentate boryl ligands enabling a highly active iridium catalyst for C–H borylation

Boryl ligands play a very important role in catalysis because of their very high electron-donating property. In this paper, NNB-type boryl anions were designed as tridentate ligands to promote aryl C–H borylation. In combination with [IrCl(COD)]2/su

Double N,B-Type Bidentate Boryl Ligands Enabling a Highly Active Iridium Catalyst for C-H Borylation

Boryl ligands hold promise in catalysis due to their very high electron-donating property. In this communication double N,B-type boryl anions were designed as bidentate ligands to promote an sp2 C-H borylation reaction. A symmetric pyridine-con

Microwave-assisted, Ir-catalyzed aromatic C-H borylation

One-step conversions of 1,3-disubstituted benzenes to aryl boronates and 2,6-disubstituted pyridines to heteroaryl boronates are described. Microwave heating was used for all reactions. [(COD)Ir(μ-OMe)]2 and 4,4′-di-tert-butyl-2,2′-bipyridine w

Sterically controlled alkylation of arenes through iridium-catalyzed C-H borylation

Complementary chemistry: A one-pot method for the site-selective alkylation of arenes controlled by steric effects is reported. The process occurs through Ir-catalyzed C-H borylation, followed by Pd- or Ni-catalyzed coupling with alkyl electrophiles. This selectivity complements that of the typical Friedel-Crafts alkylation; meta-selective alkylation of a broad range of arenes with various electronic properties and functional groups occurs in good yield with high site selectivity. Copyright

NOVEL TETRADENTATE PLATINUM COMPLEXES

Novel phosphorescent tetradentate platinum (II) compounds comprising a twisted aryl group are provided. Also provided are novel phosphorescent tetradentate platinum (II) compounds comprising an imidazo[1,2-f]phenanthridine moiety. The compounds may be used in organic light emitting devices to provide improved device efficiency, line shape and lifetime.

Cyanation of arenes via iridium-catalyzed borylation

We report a method to conduct one-pot meta cyanation of arenes by iridium-catalyzed C-H borylation and copper-mediated cyanation of the resulting arylboronate esters. This process relies on a method to conduct the cyanation of arylboronic esters, and conditions for this new transformation are reported. Conditions for the copper-mediated cyanation of arylboronic acids are also reported. By the resulting sequence of borylation and cyanation, 1,3-disubstituted and 1,2,3-trisubstituted arenes and heteroarenes containing halide, ketone, ester, amide, and protected alcohol functionalities are converted to the corresponding meta-substituted aryl nitriles. The utility of this methodology is demonstrated through the conversion of a protected 2,6-disubstituted phenol to 4-cyano-2,6-dimethylphenol, which is an intermediate in the synthesis of the pharmaceutical etravirine. The utility of the method is further demonstrated by the conversion of 3-chloro-5-methylbenzonitrile, produced through the one-pot C-H borylation and cyanation sequence, to the corresponding 3,5-disubstituted aldehydes, ketones, amides, carboxylic acids, tetrazoles, and benzylamines.

A one-pot, single-solvent process for tandem, catalyzed C-H borylation-Suzuki-Miyaura cross-coupling sequences

Methyl tert-butyl ether is a suitable solvent for iridium-catalyzed C-H borylation followed, in the same pot, by palladium-catalyzed Suzuki-Miyaura cross-coupling sequences, giving high yields of biaryls. Georg Thieme Verlag Stuttgart.

Conversion of 1,3-disubstituted arenes to chiral α,α-diaryl methylammonium chlorides using arene borylation

A two-step conversion of 1,3-disubstituted arenes to chiral α,α-diaryl methylammonium chlorides is described. In this procedure, arenes are converted to aryl boronic esters by iridium-catalyzed borylation, and the aryl boronic esters are converted to enantioenriched amines by subsequent rhodium-catalyzed addition to chiral tert-butanesulfinimes.

Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate

The borylation of arenes leads to the formation of synthetically versatile products from unactivated arene reagents. We report that Ir(I) precursors in conjunction with bipyridine ligands catalyze in high yields the borylation of arenes under mild conditions. These reactions encompase arenes bearing both electron-withdrawing and electron-donating substituents. The temperatures required for the transformation are much lower than those previously reported for direct arene borylation. The combination of [Ir(COE)2Cl]2 and (4,4-di-t-butyl)bipyridine even allows for reaction at room temperature. The same catalyst system at 100 °C provides remarkably high turnover numbers for a hydrocarbon functionalization process. Mechanistic studies show that the reactions involve uncommon, Ir(II) tris-boryl complexes. An example of this type of complex ligated by di-t-butylbipyridine was isolated and structurally characterized. It reacted rapidly at room temperature to produce aryl boronate esters in high yields. Copyright