174090-36-9

Usage

Uses

Used in Pharmaceutical Research:
4,4,5,5-tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolane is used as a valuable building block for the production of various functional molecules in pharmaceutical research. It aids in the development of new drugs and therapeutic agents.
Used in Agrochemical Development:
In the agrochemical industry, 4,4,5,5-tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolane is used as a key intermediate in the synthesis of various agrochemicals, contributing to the development of effective pesticides and other agricultural products.
Used in Materials Science:
4,4,5,5-tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolane is utilized as an important tool in materials science for the creation of advanced materials with specific properties, such as polymers, composites, and coatings. Its use in this field helps to enhance the performance and functionality of these materials.

Upstream product

• 100-42-5 styrene 
• 73183-34-3 bis(pinacol)diborane 
• 100-41-4 ethylbenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 585-71-7 (1-bromoethyl)benzne 
• 100-52-7 benzaldehyde 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 24182-83-0 (E)-styryl(p-tolyl)sulfane 
• 592-41-6 1-hexene 
• 1333-74-0 hydrogen 
• 143825-84-7 4,4,5,5-tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane 
• 672-65-1 (1-chloroethyl)benzene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 90002-36-1 2-ethylphenyl boronic acid 

Downstream Products

• 7782-24-3 (S)-2-Phenylpropionic acid 
• 7782-26-5 (R)-2-Phenylpropionic acid 
• 1123-85-9 (RS)-2-phenyl-1-propanol 
• 98-85-1 1-Phenylethanol 
• 2722-36-3 3-phenyl-1-butanol 
• 19967-24-9 4-phenylpentan-1-ol 
• 1142813-45-3 (R)-1-phenyl-1-(2-methylphenyl)ethane 
• 1142813-41-9 (R)-1-(p-chlorophenyl)-1-phenylethane 
• 1142813-46-4 (S)-1-chloro-4-(1-phenylethyl)benzene 
• 1142813-40-8 (R)-1-(4-(1-phenylethyl)phenyl)ethan-1-one 
• 130065-37-1 (S)-1-(4-(1-phenylethyl)phenyl)ethan-1-one 
• 1142813-42-0 (R)-1-phenyl-1-(4-methylphenyl)ethane 
• 1142813-47-5 (S)-1-methyl-4-(1-phenylethyl)benzene 
• 60492-48-0 (R)-1-(4-methoxyphenyl)-1-phenylethane 

Relevant academic research and scientific papers

Electrosynthesis of benzylboronic acids and esters

A novel preparation of benzylboronic acids and esters is described by using an electrochemical reductive coupling reaction between benzylic halides and borating agents (trialkylborates or pinacolborane). The reaction is carried out at room temperature in DMF or THF with the use of a sacrificial magnesium anode in a single-compartment cell.

Catalytic activity of phosphine - Copper complexes for hydroboration of styrene with pinacolborane: Experiment and theory

We have carried out density functional theory calculations as well as experiments to rationalize the catalytic activity of various phosphine-copper complexes for the hydroboration of styrene with pinacolborane. The experimentally obtained catalytic efficiency was explained on the basis of activation barriers for consecutive reaction mechanism steps as well as by molecular orbitals and charges in the transition state. Bidentate ligands were found to be more efficient than monodentate ligands for catalytic activity. Bidentate ligands make the reactant complexes less stable than monodentate ligands due to steric hindrance. This information could be usefully utilized for new catalysts design. The calculated kinetic data were consistent with the experimental conversion efficiency in a process that was hypothesizd to undergo the addition of Cu - H to styrene as the rate-limiting step. From the electronic distribution of the HOMO and the charge of the copper atom in the transition state, it was found that styrenes substituted with electron withdrawing groups would give higher conversions, and the catalytic efficiency could be increased with properly designed electron-donating ligands for the copper catalyst complex.

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.

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.

Rhodium-Catalyzed Regiodivergent Synthesis of Alkylboronates via Deoxygenative Hydroboration of Aryl Ketones: Mechanism and Origin of Selectivities

Here, we report an efficient rhodium-catalyzed deoxygenative borylation of ketones to synthesize alkylboronates, in which the regioselectivity can be switched by the choice of the ligand. The linear alkylboronates were obtained exclusively in the presence of P(nBu)3, and PPh2Me favored the formation of branched alkylboronates. The protocol also allows access to 1,1,2-triboronates from the readily available ketones. Mechanistic studies suggest that this Rh-catalyzed deoxygenative borylation of ketones goes through an alkene intermediate, which undergoes regiodivergent hydroboration to afford linear and branched alkylboronates. The different steric effects of PPh2Me and P(nBu)3 were found to be responsible for product selectivity by density functional theory calculations. The alkene intermediate can alternatively undergo sequential dehydrogenative borylation and hydroboration to deliver the triboronates.

Selective electrocatalytic hydroboration of aryl alkenes

Organoboron compounds are powerful precursors of value-added organic compounds in synthetic chemistry, and transition metal-catalysed borylation has always been dominant. To avoid toxic reagents and costs associated with metal catalysts, simpler, more eco

Practical Synthesis of Allyl, Allenyl, and Benzyl Boronates through SN1′-Type Borylation under Heterogeneous Gold Catalysis

Efficient borylation of sp3 C-O bonds by supported Au catalysts is described. Au nanoparticles supported on TiO2 showed high activity under mild conditions employing low catalyst loading conditions without the aid of any additives, such as phosphine and bases. A variety of allyl, propargyl, and benzyl substrates participated in the heterogeneously catalyzed reactions to furnish the corresponding allyl, allenyl, and benzyl boronates in high yields. Besides, Au/TiO2 was also effective for the direct borylation of allylic and benzylic alcohols. A mechanistic investigation based on a Hammett study and control experiments revealed that sp3 C-O bond borylation over supported Au catalysts proceeded through SN1′-type mechanism involving the formation of a carbocationic intermediate. The high activity, reusability, and environmental compatibility of the supported Au catalysts as well as the scalability of the reaction system enable the practical synthesis of valuable organoboron compounds.

Manganese-Catalyzed Hydroboration of Terminal Olefins and Metal-Dependent Selectivity in Internal Olefin Isomerization-Hydroboration

In the past decade, the use of earth-abundant metals in homogeneous catalysis has flourished. In particular, metals such as cobalt and iron have been used extensively in reductive transformations including hydrogenation, hydroboration, and hydrosilylation

(o-Phenylenediamino)borylstannanes: Efficient Reagents for Borylation of Various Alkyl Radical Precursors

(o-Phenylenediamino)borylstannanes were newly synthesized to achieve radical boryl substitutions of a variety of alkyl radical precursors. Dehalogenative, deaminative, decharcogenative, and decarboxylative borylations proceeded in the presence of a radica

1-D manganese(ii)-terpyridine coordination polymers as precatalysts for hydrofunctionalisation of carbonyl compounds

Reductive catalysis with earth-abundant metals is currently of increasing importance and shows potential in replacing precious metal catalysis. In this work, we revealed catalytic hydroboration and hydrosilylation of ketones and aldehydes achieved by a structurally defined manganese(ii) coordination polymer (CP) as a precatalyst under mild conditions. The manganese-catalysed methodology can be applied to a range of functionalized aldehydes and ketones with turnover numbers (TON) of up to 990. Preliminary results on the regioselective catalytic hydrofunctionalization of styrenes by the Mn-CP catalyst are also presented.