4406-72-8

Upstream product

• 107-21-1 ethylene glycol 
• 1061180-99-1 (4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate 
• 3262-89-3 triphenylboroxine 
• 504-63-2 trimethyleneglycol 
• 98-80-6 phenylboronic acid 
• 108-86-1 bromobenzene 
• 873-51-8 phenylborondichloride 
• 960-71-4 triphenylborane 

Downstream Products

• 591-50-4 iodobenzene 
• 118097-60-2 benzyl 3-phenylbutenoate 
• 338461-66-8 (R)-N-benzyl-3-phenylbutanamide 
• 426841-80-7 (1R,2S)-cis-2-phenyl-1,2-dihydronaphthalen-1-ol 
• 220616-20-6 1,4-diphenylpiperidine 
• 62787-21-7 3,5-di-tert-butylphenyl phenyl ether 
• 92-91-1 biphenyl-4-acetaldehyde 
• 57344-86-2 (S)-3-phenylcyclohexanone 
• 6914-98-3 2-phenylbenzo[de]isoquinoline-1,3-dione 
• 95843-97-3 2,4-dimethyl-2,4-pentanediol phenylboronic ester 
• 4406-75-1 phenylboronic acid 1,2-propanediol ester 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 6638-70-6 (3aR,7aS)-2-phenyl-hexahydro-2H-1,3,2-benzodioxaborole 

Relevant academic research and scientific papers

Boron trifluoride facilitated transesterification of dioxaborolanes

The direct transesterification of dioxaborolanes (alkane-1,2-diol based boronate esters) was explored. Using BF3·OEt2, alkane-1,2-diol based mono- and bis-boronate esters (i.e., pinacol and ethylene glycol) have been converted quantitatively to either benzene-1,2-diol or alkane-1,3-diol based boronate esters. In the case of pinacol esters, esterification is facilitated by the accompanying pinacol rearrangement, thus shifting the reaction equilibrium.

Insight into Copper Catalysis: In Situ Formed Nano Cu2O in Suzuki-Miyaura Cross-Coupling of Aryl/Indolyl Boronates

A ligand-free copper catalyzed Suzuki-Miyaura coupling of 3,5-diiodopyridine with aryl and indole boronates has been explored in good to excellent yields. In situ generation of nano-Cu2O from CuCl2 under the reaction conditions has been discovered for the first time. The generality of the reaction was further demonstrated by the arylation of 5-iodopyrimidine, iodopyridines, iodobenzenes, and diiodobenzenes and resulted in good to moderate yields. Moreover, bisindole alkaloid Scalaridine A has been successfully synthesized in 60% overall yield.

Palladium-Catalyzed Suzuki Reactions in Water with No Added Ligand: Effects of Reaction Scale, Temperature, pH of Aqueous Phase, and Substrate Structure

The heterogeneous palladium-catalyzed Suzuki reactions between model aryl bromides (4-bromoanisole, 4-bromoaniline, 4-amino-2-bromopyridine, and 2-bromopyridine) and phenylboronic acid have been successfully conducted in water with no added ligand at the 100 mL scale using 20-40 mmol of aryl bromide. The product yields associated with these substrates were optimized, and key reaction parameters affecting the yields were identified. The results clearly indicate that the reaction parameters necessary to achieve high yields are substrate-dependent. In addition, it is demonstrated that aqueous Suzuki reactions of substrates containing basic nitrogen centers can produce quantitative yields of desired products in the absence of added ligand.

Superstable palladium(0) complex as an air-and thermostable catalyst for Suzuki coupling reactions

An unprecedentedly thermo-and air-stable Pd0 complex from readily available electron-poor trifluoromethylated phosphine was serendipitously discovered. As detailed and comparative DFT calculations indicate, the stability of the complex is associated with unusually strong ligand-ligand noncovalent interactions. The unique stability and the presence of hydrophobic structural elements of the complex offer several practical advantages, which were exploited in catalytic Suzuki-Miyaura coupling reactions.

Seven-membered ring boronates at trans-diol moieties of carbohydrates

MS and 1H, 13C and 11B NMR results are presented revealing the formation of cyclic seven-membered boronate structures at trans-1,2-diol moieties of carbohydrates providing new opportunities for the activation, protection and analysis of glucopyranose-based oligomers and polymers such as cellulose or starch. 'Coordination-induced shifts' in 13C NMR spectra were identified for the esterification by boronic acids of carbohydrates, which can be applied for further studies.

Aerobic alcohol oxidation coupled to palladium-catalyzed alkene hydroarylation with boronic esters

(Chemical Equation Presented) An oxidation exercise: An aerobic alcohol oxidation coupled with a regioselective palladium-catalyzed reductive functionalization of styrenes and arylboronic esters has been developed (see scheme). The mechanism is thought to proceed by initial oxidation of the solvent to generate a PdII-hydride species, which subsequently reacts with the alkene and arylboronic ester to ultimately generate a new C-C bond.

A comparative study of the relative stability of representative chiral and achiral boronic esters employing transesterification

A comparative study of the transesterification of five representative chiral and achiral boronic esters with various structurally modified diols was undertaken to qualitatively understand the factors influencing the relative stability of these boronic esters. Several factors such as chelation, conformation, steric bulk of the substituents, size of the heterocycle, and entropy influence the relative rate of transesterification as well as the stability of the boronic esters. Amongst these boronic esters, pinanediol phenylboronic ester was found to be the most stable boronic ester whereas DIPT boronic ester appeared to be thermodynamically the least stable one. The transesterification with sterically hindered diols was observed to be relatively slow, but afforded thermodynamically more stable boronic esters. Boronic esters derived from cis-cyclopentanediols and the bicyclo[2.2.1]heptane-exo,exo-2,3- diols are relatively more stable. This study not only presents the qualitative picture of relative stability of various boronic esters, but also provides helpful hints regarding the possible recovery of chiral auxiliaries. Many C 2-symmetric chiral auxiliaries, such as 2,3-butanediol, 2,4-pentanediol, DIPT, and cis-cyclohexane-1,2-diol, can be retrieved by simple transesterification of the corresponding boronic esters with commercial inexpensive diols, such as pinacol, 1,3-propanediol, and neopentyl glycol.

Hydrolytically-Resistant Boron-Containing Therapeutics And Methods Of Use

Compositions and methods of use of boron derivatives, including benzoxaboroles, benzazaboroles and benzthiaboroles, as therapeutic agents for treatment of diseases caused by fungi, yeast, bacteria or viruses are disclosed, as well as methods for synthesis of said agents and compositions thereof.

Compounds for the Treatment of Periodontal Disease

Compounds, compositions and methods are provided which are useful in the treatment of periodontal disease.

Stability of boronic esters - Structural effects on the relative rates of transesterification of 2-(phenyl)-1,3,2-dioxaborolane

Relative rates of reaction of the achiral cyclic phenylboronic ester 2-(phenyl)-1,3,2-dioxaborolane with a wide variety of structurally modified diols, have been studied to understand the factors influencing the relative stabilities of boronic esters. It is found that the alkyl substituents on the α-carbons of diols slow down the transesterification, but produce thermodynamically more stable boronic ester. Six-membered boronic esters are thermodynamically more stable than their corresponding five-membered analogs. Amongst cyclic 1,2-diols, cis-1,2-cyclopentanediol displaces ethylene glycol instantaneously whereas trans-1,2-cyclopentanediol is totally unreactive, which suggests that the cis-stereochemistry of the 1,2-diol is a prerequisite for transesterification. Among the 1,5-diols, diethanolamine displaces ethylene glycol quite rapidly forming a more stable bicyclic chelate in which nitrogen is attached to boron by a coordinating bond (as evident by 11B NMR spectroscopy). The oxygen atom of di(ethylene glycol) and the sulfur atom of 2,2′-thiodiethanol do not assist in displacing the ethylene glycol from their boronic esters.