214360-78-8

Usage

Uses

Used in Pharmaceutical Synthesis:
2,4,6-Trimethylbenzeneboronic acid neopentyl glycol cyclic ester is used as a key intermediate in the synthesis of pharmaceuticals for its ability to facilitate the construction of complex organic molecules. Its unique boron-containing structure allows for the development of new drugs with enhanced properties and therapeutic effects.
Used in Agrochemical Development:
In the agrochemical industry, 2,4,6-Trimethylbenzeneboronic acid neopentyl glycol cyclic ester is used as a precursor in the synthesis of various agrochemicals. Its reactivity and structural features contribute to the creation of novel compounds with improved efficacy in crop protection and pest management.
Used in Material Science:
2,4,6-Trimethylbenzeneboronic acid neopentyl glycol cyclic ester is employed as a building block in material science for the development of new materials with specific properties. Its incorporation into the molecular structure of these materials can lead to advancements in areas such as polymer science, nanotechnology, and materials engineering.
Used in Organic Synthesis and Catalysis:
As a cyclic boronic ester, 2,4,6-Trimethylbenzeneboronic acid neopentyl glycol cyclic ester is used as a reagent in organic synthesis and catalysis. Its unique reactivity allows for the formation of new chemical bonds and the transformation of organic substrates, facilitating the synthesis of complex organic compounds and the development of novel catalytic processes.

InChI:InChI=1/C14H21BO2/c1-10-6-11(2)13(12(3)7-10)15-16-8-14(4,5)9-17-15/h6-7H,8-9H2,1-5H3

Upstream product

• 576-83-0 2,4,6-trimethylphenyl bromide 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 69464-76-2 2,4,6-(trimethylphenyl)dichloroborane 
• 23822-17-5 tris(2,4,6-trimethylphenyl)antimony 
• 5980-97-2 mesitylboronic acid 

Downstream Products

• 1421030-00-3 4-phenyl-3-(3,5-bis(2,4,6-trimethylphenyl)phenyldiazenyl)pyridine 
• 137129-03-4 N,N-dibenzyl-2,4,6-trimethylaniline 
• 502622-88-0 4′-(2,4,6-trimethylphenyl)-2,2′:6′,2″-terpyridine 
• 121-98-2 methyl 4-methoxybenzoate 
• 23676-08-6 methyl 4-ethoxybenzoate 
• 480-63-7 mesitylenecarboxylic acid 

Relevant academic research and scientific papers

The steric aryl boric acid ester preparation method of the compound

The invention discloses a preparation method of a high-sterically-hindered arylborate compound. The preparation method includes following steps: in the presence of a catalyst of a catalyst tri(dibenzalacetone)dipalladium with a phosphine ligand (wherein the phosphine ligand is 3-diphenylphosphine-2-(2,6-dimethoxylphenyl)-N-methylindole), adding an aryl chloride, bis(neopentyl glycolato)diboron, and an additive ceseium acetate to a 1,4-dioxane solution; and carrying out a reaction at 100-130 DEG C for 12-48 hours to obtain the arylborate compound. In the invention, the employed substrate is stable, is low in cost and is easy to obtain and the catalyst is unique, is easy to prepare and is suitable for the reaction of the high-sterically-hindered aryl chloride. The system is compatible of existences of functional groups, such as an ester group, an aldehyde group, methoxyl and the like so that range of the substrate is greatly developed. The catalyst system is stable, is high in catalytic activity, is wide in suitable scope, is good in selectivity and is mild in reaction conditions. The high-sterically-hindered arylborate compound can be widely applied in cross coupling reaction catalyzed by transition metal, thereby preparing various compounds, such as biaromatic hydrocarbons. The preparation method has a great application potential in synthesis of natural medicines and drug intermediates.

Synthesis of arylboronates by boron-induced ipso-deantimonation of triarylstibanes with boron trihalides and its application in one-pot two-step transmetallation/cross-coupling reactions

The reaction of triarylstibanes (1) with boron trihalides (BCl3, and BBr3) afforded arylboron dihalides (2) by utilizing all the three aryl groups on the antimony. Boron intermediates (2) were transformed to arylboronates (3) in good to excellent yields by treatment with methanol and 1,3-propanediol. Further, the Pd-catalyzed reactions of 2 with organic halides such as 1-bromonaphthalene and benzoyl chloride in the presence of H2O afforded the corresponding cross-coupling products, unsymmetrical biaryls (4) and ketones (5), in moderate to good yields. The potential energy surfaces for the transmetallations of triarylstibanes (1) with BCl3 affording 2 were determined by molecular orbital calculations. The analyses of substituent effects on theoretically calculated reactivities showed the importance of the resonance effects of the ring substituents on these transmetallations.

C-H activation by amide chelation control: Ruthenium-catalyzed direct synthesis of 2-Aryl-3-furanamides

A new, catalytic methodology for the synthesis of heterobiaryls by the ruthenium-catalyzed C-H activation/cross-coupling of heterocyclic amides with aryl boroneopentylates is surveyed. From this survey, the highly regioselective reaction of furan-3-carboxamide to give 2-aryl-3-furanamides is optimized and generalized in scope with respect to the aryl boroneopentylate coupling partners. Established thereby is a one-step synthetic method which may supercede the broadly applied two-step directed ortho metalation (DoM)-cross coupling reaction involving cryogenic and strong base conditions and which has potential for further ortho and remote metalation chemistry.

Beyond directed ortho metalation: Ruthenium-catalyzed amide-directed C Ar-N activation/C-C coupling reaction of anthranilamides with organoboronates

A new, catalytic, and general methodology for the synthesis of biaryls and heterobiaryls by the cross coupling of anthranilamide derivatives (o-NMe 2 benzamides) with aryl boroneopentylates is described. The reaction proceeds under catalytic RuH2(CO)(PPh3)3 conditions driven by the activation of the unreactive C-N bond by amide directing group (DG)-Ru catalyst chelation. High regioselectivity, orthogonality with the Suzuki-Miyaura reaction, operational simplicity, and convenient scale-up are features of these reactions which may lend themselves to industrial applications.

Beyond directed ortho metalation: Ru-catalyzed CAr-O activation/cross-coupling reaction by amide chelation

Disclosed is a new, catalytic, and general methodology for the chemical synthesis of biaryl, heterobiaryl, and polyaryl molecules by the cross-coupling of o-methoxybenzamides with aryl boroneopentylates. The reaction is based on the activation of the unreactive C-OMe bond by the proximate amide directing group using catalytic RuH2(CO)(PPh3)3 conditions. A one-step, base-free coupling process is thereby established that has the potential to supersede the useful two-step directed ortho metalation/cross- coupling reaction involving cryogenic temperature and strong base conditions. High regioselectivity, orthogonality with the Suzuki-Miyaura reaction, operational simplicity, minimum waste, and convenient scale-up make these reactions suitable for industrial applications.

Simple base-free Miyaura-type borylation of triarylantimony diacetates with tetra(alkoxo)diborons under aerobic conditions

The reaction of triarylantimony diacetates with tetra(alkoxo)diborons in the presence of PdCl2(PPh3)2 (1 mol%) catalyst resulted in the Miyaura-type B-arylation to form arylboronates in moderate to good yields under base-free conditions. In the present reaction, two of the three aryl groups of antimony reagent were transferred to the coupling products when the reaction was carried out under aerobic conditions, although only one of the three aryl group of the antimony reagent was involved under an argon atmosphere. The broad scope of the reaction was demonstrated by using a variety of triarylantimony diacetates with sterically hindered aryl groups and highly reactive p-bromo-functionalized aryl derivatives.

Photocontrol over cooperative porphyrin self-assembly with phenylazopyridine ligands

The cooperative self-assembly of chiral zinc porphyrins is regulated by a photoresponsive phenylazopyridine ligand (1; see picture). Porphyrin stacks depolymerize into dimers upon axial ligation and the strength of the coordination is regulated by its pho

Copper-catalyzed amination of arylboronates with N,N-dialkylhydroxylamines

A tolerant coupling: The title reaction has been developed to deliver arylamines (see scheme; Bz=benzoyl, dppbz=1,2-bis(diphenylphosphino)benzene). The catalysis is based on electrophilic, umpolung amination and enables the use of secondary acyclic amines. Various functional groups are tolerated, thus opening up a new substrate class for the Chan-Lam-type coupling.

Carboxylation of organoboronic esters catalyzed by N-heterocyclic carbene copper(I) complexes

Copper complexes with a CO2 fixation: Copper(I) complexes serve as excellent catalysts for the carboxylation of aryl- and alkenylboronic esters with CO2, affording a variety of functionalized carboxylic acid derivatives (see scheme). Important active intermediates such as the copper(I) aryl and carboxylate complexes, [(IPr)CuR] and [(IPr)CuOCOR] (R = 4-MeOC 6H4, IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2- ylidene), are isolated and structurally characterized. (Chemical Equation Presented).