92152-56-2

Upstream product

• 25062-46-8 4-bromobenzaldehyde oxime 
• 100-51-6 benzyl alcohol 
• 586-76-5 4-Bromobenzoic acid 
• 108-88-3 toluene 
• 586-75-4 4-chlorobenzoyl chloride 
• 1024-41-5 benzyl tosylate 
• 1122-91-4 4-bromo-benzaldehyde 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 873-75-6 4-bromobenzenemethanol 
• 99-90-1 para-bromoacetophenone 
• 58824-56-9 1-(p-bromophenyl)prop-2-en-1-ol 
• 14367-97-6 1-(4-bromophenyl)-2-nitro-1-ethanone 

Downstream Products

• 120-51-4 benzoic acid benzyl ester 
• 134078-95-8 4-Trimethylsilanyl-benzoic acid benzyl ester 
• 134078-93-6 4-Tributylstannanyl-benzoic acid benzyl ester 
• 134078-97-0 Biphenyl-4,4'-dicarboxylic acid dibenzyl ester 
• 586-76-5 4-Bromobenzoic acid 
• 1383435-89-9 benzyl 4-(2,3-dihydro-1H-inden-1-yl)benzoate 
• 1421009-29-1 2'-hydroxy-5'-methyl-[1,1':3',1-terphenyl]-4,4-dicarboxylic acid dibenzyl ester 
• 1421009-32-6 C₃₇H₃₂O₆ 
• 1566593-61-0 2-((4-bromobenzyl)oxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 345964-87-6 1-bromo-4-(1-benzyloxyvinyl)-benzene 

Relevant academic research and scientific papers

Hydrogen bond-directed assembly of silsesquioxanes cubes: synthesis of carboxylic acid POSS derivatives and the solid state structure of octa[2-(p-carboxyphenyl)ethyl] silsesquioxane

The octa[2-(p-carboxyphenyl)ethyl] and octa[2-(4-carboxy-1,1′-biphenyl)ethyl] silsesquioxane were synthesised under mild reaction conditions upon hydrogenolysis of the corresponding benzyl-ester derivatives. The octa[2-(p-carboxyphenyl)ethyl] silsesquioxane was shown to self-assemble upon formation of carboxylic acid dimers. The presence of eight carboxylic acid functional groups allowed to obtain an ordered silsesquioxane hybrid network. The X-ray crystal structures of the octa-ester and of the octa-acid were determined. The three-dimensional conformation of the ester provided an interpenetrated compact packing of the molecular building blocks without any specific supramolecular interaction. The two-dimensional character of the acid and the directionality of the hydrogen bond pattern of a dimer of acid led to the formation of hydrogen-bonded ribbons. It showed that functionalized silsesquioxane precursors capable of hydrogen bonding are of interest to generate nanostructured materials through self-organization processes. Moreover, the use of carboxylic acid groups is interesting not only because of their ability to form carboxyl dimer structures by hydrogen bonding but also because of their ability to form metal carboxylate derivatives that may lead to new organised hybrid metal organic silica frameworks.

Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters

A cheap, facile and metal-free photochemical protocol for the activation of aromatic aldehydes has been developed. Utilizing thioxanthen-9-one as the photocatalyst and cheap household lamps as the light source, a variety of aromatic aldehydes have been activated and subsequently converted in a one-pot reaction into amides, hydroxamic acids and esters in good to high yields. The applicability of this method was highlighted in the synthesis of Moclobemide, a drug against depression and social anxiety. Extended and detailed mechanistic studies have been conducted, in order to determine a plausible mechanism for the reaction.

Iodine-catalyzed synthesis of β-uramino crotonic esters as well as oxidative esterification of carboxylic acids in choline chloride/urea: a desirable alternative to organic solvents

Abstract: Iodine-mediated selective synthesis of β-uramino crotonic esters was achieved via the reaction of β-dicarbonyls and urea at room temperature. Choline chloride/urea mixture, as an eco-friendly, cheap, non-toxic, and recyclable deep eutectic solvent (DES), was employed as sustainable media as well as reagent at the same time in these transformations. Some derivatives of β-uramino crotonic esters were synthesized with good to high yields without a tedious work-up. The process could be done to synthesize the above-mentioned compounds in gram scale. Moreover, oxidative cross-esterification of carboxylic acids with alkyl benzenes was carried out in the above-mentioned DES by the employment of tetrabutylammonium iodide (TBAI) as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant at 80?°C. DES/TBAI system was reused up to five consecutive times. Graphic abstract: Iodine-catalyzed C–N and C–O bond formation in choline chloride/urea as a green solvent under the mild reaction conditions. Providing the clean procedure toward synthesis of β-uramino crotonic esters and benzylic esters.[Figure not available: see fulltext.].

Acetyl nitrate mediated conversion of methyl ketones to diverse carboxylic acid derivatives

The development of a novel acetyl nitrate mediated oxidative conversion of methyl ketones to carboxylic acid derivatives is described. By analogy to the haloform reaction and supported by experimental and computational investigation we propose a mechanism for this transformation.

Benzyne-Mediated Esterification Reaction

A benzyne-mediated esterification of carboxylic acids and alcohols under mild conditions has been realized, which is made possible via a selective nucleophilic addition of carboxylic acid to benzyne in the presence of alcohol. After a subsequent transesterification with alcohol, the corresponding esters can be produced efficiently. This benzyne-mediated protocol can be used on the modification of Ibuprofen, cholesterol, estradiol, and synthesis of nandrolone phenylpropionate. In addition, benzyne can also be used to promote lactonization and amidation reaction.

Bu 4 NI-Catalyzed C-C Bond Cleavage and Oxidative Esteri??cation of Allyl Alcohols with Toluene Derivatives

A novel oxidative esterification of 1-arylprop-2-en-1-ols with toluene derivatives catalyzed by tetrabutylammonium iodide (TBAI) is reported. The optimization of the reaction conditions illustrates that each of experiment parameters including the catalyst, solvent, and oxidant is significant for present oxidative functionalization. This metal-free protocol has a broad substrate scope including the halogen groups for further functionalization and enriches the reactivity profile of allyl alcohol and toluene derivatives. In addition, this protocol represents a new transformation of allyl alcohol involving C-C bond cleavage and C-O bond forming.

Spatially Resolved Covalent Functionalization Patterns on Graphene

Spatially resolved functionalization of 2D materials is highly demanded but very challenging to achieve. The chemical patterning is typically tackled by preventing contact between the reagent and material, which brings various accompanying challenges. Photochemical transformation on the other hand inherently provides remote high spatiotemporal resolution using the cleanest reagent—a photon. Herein, we combine two competing reactions on a graphene substrate to create functionalization patterns on a micrometer scale via the Mitsunobu reaction. The mild reaction conditions allow introduction of covalently dynamic linkages, which can serve as reversible labels for surface- or graphene-enhanced Raman spectroscopy characterization of the patterns prepared. The proposed methodology thus provides a pathway for local introduction of arbitrary functional groups on graphene.

Formation of esters and amides via metal-free Csp2-Csp3 bond cleavage of α-nitro ketone: Mechanistic insight to the reaction pathway

A catalyst free protocol for hucleophilic Csp2-Csp3 bond cleavage of a-nitroketone has been achieved for the formation of C-O and C-N bond. A series of differently substituted a-nitroketones could be selectively cleaved and converted into corresponding esters and tosylamides in presence of alcohols and bromamine-T respectively. Mechanism of the C-C bond cleavage has been proposed by identifying different reaction intermediates using IR and NMR spectroscopic methods.

Oxidation-Reduction Condensation of Diazaphosphites for Carbon-Heteroatom Bond Formation Based on Mitsunobu Mechanism

An efficient oxidation-reduction condensation reaction of diazaphosphites with various nonacidic pronucleophiles in the presence of DIAD as a weak oxidant has been developed for carbon-heteroatom bond formation. This mild process affords structurally diverse tertiary amines, secondary amines, esters, ethers, and thioethers in moderate to excellent yields. The selective synthesis of secondary amines from primary amines has been achieved. Importantly, a practical application to the synthesis of antiparkinsonian agent piribedil has been demonstrated.

Mitsunobu Reaction Using Basic Amines as Pronucleophiles

A novel protocol for extending the scope of the Mitsunobu reaction to include amine nucleophiles to form C-N bonds through the utilization of N-heterocyclic phosphine-butane (NHP-butane) has been developed. Both aliphatic alcohols and benzyl alcohols are suitable substrates for C-N bond construction. Various acidic nucleophiles such as benzoic acids, phenols, thiophenol, and secondary sulfonamide also provide the desired products of esters, ethers, thioether, and tertiary sulfonamide with 43-93% yields. Importantly, C-N bond-containing pharmaceuticals, Piribedil and Cinnarizine, have been synthesized in one step from the commercial amines under this Mitsunobu reaction system.