20627-49-0

Upstream product

• 501-52-0 3-Phenylpropionic acid 
• 71-36-3 butan-1-ol 
• 71-43-2 benzene 
• 592-84-7 n-butyl formate 
• 201230-82-2 carbon monoxide 
• 688-74-4 boric acid tributyl ester 
• 103-63-9 1-phenyl-2-bromoethane 
• 65439-56-7 3-phenyl-1-(2-thioxothiazolidin-3-yl)propan-1-one 
• 104-53-0 3-phenyl-propionaldehyde 
• 67-56-1 methanol 
• 592-76-7 1-Heptene 
• 100-42-5 styrene 
• 141-32-2 acrylic acid n-butyl ester 
• 109-65-9 1-bromo-butane 

Downstream Products

• 2021-28-5 ethyl dihydrocinnamate 
• 13326-06-2 n-propyl 3-phenylpropionate 
• 232949-65-4 pentyl 3-phenylpropionoate 
• 51816-46-7 N‐(2‐hydroxyethyl)‐3‐phenylpropanamide 
• 17428-96-5 1,1-d2-3-phenylpropan-1-ol 
• 37826-57-6 1-octyl 3-phenylpropanoate 
• 122-97-4 3-Phenyl-1-propanol 

Relevant academic research and scientific papers

Kinetics and mechanism of styrene hydrocarboalkoxylation catalyzed by Pd° complex in the presence of toluenesulfonic acid

The kinetics of the catalytic reaction of styrene with CO and n-butanol in the Pd(dba)2 - TsOH - Ph3P system in dioxane (383 K) was studied. The initial rates of accumulation of regioisomeric products (butyl 2-and 3-phenylpropionates) were measured as functions of the CO pressure, reactant concentrations, and the catalytic system components. A kinetic model of the process and a hydride mechanism with the HPd(Ph3P)3+ cationic complex acting as a key intermediate were proposed.

Convenient synthesis of poly(butylene succinate) catalyzed by distannoxane

A convenient method for the synthesis of poly(butylene succinate) (1) of high molecular weight has been developed. This polyester was prepared readily by the distannoxane-catalyzed polycondensation of succinic acid (2) with 1,4-butanediol (3) in decalin a

Selective Reduction of Carboxylic Acids to Alcohols in the Presence of Alcohols by a Dual Bulky Transition-Metal Complex/Lewis Acid Catalyst

Here, we report a molecular method for the generally applicable reduction of mono-and dicarboxylic acids that selectively furnishes a diverse variety of alcohols, including mono-and diols. One of the inherent drawbacks of the direct hydrogenation of carboxylic acids to alcohols is the in situ formation of the corresponding esters via condensation of the carboxylic acids with the produced alcohols. Especially, the hydrogenation of polycarboxylic acids frequently suffers from the formation of a complex mixture of oligomeric esters. This issue was successfully overcome by the combined use of a dual catalyst that consists of a bulky (PNNP)iridium complex and a Lewis acid. Owing to the steric bulk and robustness of the iridium catalyst, the main role of the Lewis acid is to independently catalyze the esterification, albeit the cooperative activation of (a resting state of) the iridium catalyst by the Lewis acid also seems to be implied.

Zr-MOF-808 as Catalyst for Amide Esterification

In this work, zirconium-based metal–organic framework Zr-MOF-808-P has been found to be an efficient and versatile catalyst for amide esterification. Comparing with previously reported homogeneous and heterogeneous catalysts, Zr-MOF-808-P can promote the reaction for a wide range of primary, secondary and tertiary amides with n-butanol as nucleophilic agent. Different alcohols have been employed in amide esterification with quantitative yields. Moreover, the catalyst acts as a heterogeneous catalyst and could be reused for at least five consecutive cycles. The amide esterification mechanism has been studied on the Zr-MOF-808 at molecular level by in situ FTIR spectroscopic technique and kinetic study.

Esterification of Tertiary Amides: Remarkable Additive Effects of Potassium Alkoxides for Generating Hetero Manganese–Potassium Dinuclear Active Species

A catalyst system of mononuclear manganese precursor 3 combined with potassium alkoxide served as a superior catalyst compared with our previously reported manganese homodinuclear catalyst 2 a for esterification of not only tertiary aryl amides, but also tertiary aliphatic amides. On the basis of stoichiometric reactions of 3 and potassium alkoxide salt, kinetic studies, and density functional theory (DFT) calculations, we clarified a plausible reaction mechanism in which in situ generated manganese–potassium heterodinuclear species cooperatively activates the carbonyl moiety of the amide and the OH moiety of the alcohols. We also revealed details of the reaction mechanism of our previous manganese homodinuclear system 2 a, and we found that the activation free energy (ΔG≠) for the manganese–potassium heterodinuclear complex catalyzed esterification of amides is lower than that for the manganese homodinuclear system, which was consistent with the experimental results. We further applied our catalyst system to deprotect the acetyl moiety of primary and secondary amines.

C-C Bond Cleavage of Unactivated 2-Acylimidazoles

2-Acylimidazoles are widely used as post-Transformable carboxylic acid equivalents in chemoselective and enantioselective reactions. Their transformations, however, require pretreatment with highly reactive, toxic methylating reagents to facilitate C-C bond cleavage. Here, we demonstrate that such pretreatment can be avoided and the C-C bond cleaved under neutral conditions without the use of additional reagents or catalysts. The scope of the reaction, including the use of products reported in the literature as substrates, and some mechanistic insights are described.

Pentamethylphenyl (Ph*) and Related Derivatives as Useful Acyl Protecting Groups for Organic Synthesis: A Preliminary Study

A study of acyl protecting groups derived from the Ph? motif is reported. While initial studies indicated that a variety of functional groups were not compatible with the Br 2-mediated cleavage conditions required to release the Ph? group, strategies involving the use of different reagents or a modification of Ph? itself (Ph*OH) were investigated to solve this problem.

Imidazolium Based Fluorous N-Heterocyclic Carbenes as Effective and Recyclable Organocatalysts for Redox Esterification

A series of new highly fluorophilic ionic liquids (f > 110) was synthetized from 3-iodopropyltris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane and N-alkyl imidazoles, followed by anion exchange. N-heterocyclic carbenes generated in situ from obtained imidazolium salts were employed to catalyze redox esterification (umpolung) of cinnamaldehyde with alcohols. The most effective N-methyl derivative with iodide as a counter anion was studied in detail with respect to the optimization of reaction conditions, substrate scope and recyclability. Recovery of the precatalyst was achieved using either fluorous extraction or performing the reaction in suitable fluorous biphase system with direct recycling of the fluorinated precatalyst phase. For both tested options, the catalytic activity did not significantly decrease within 5 subsequent cycles. The redox esterification was shown to proceed also in supercritical carbon dioxide (scCO2) as an alternative solvent where the activity of the fluorinated catalyst was also superior to the nonfluorinated model, while retaining the benefit of easy recycling.

Ionic liquid catalytic synthesis of styrene-acrylic acid ester derivative of the method (by machine translation)

The invention provides an ionic liquid catalytic synthesis of styrene-acrylic acid ester derivative of the method, the method adopts the imidazole ionic liquid as catalyst, in order to cinnamic aldehyde or its derivatives and nandrolone or testosterone alcohol or phenol derivatives as raw materials, without any additional acid and alkali, one-step reaction, to obtain the styrene-acrylic acid ester derivative. Compared with the prior art, the maximum of this invention is characterized in that the raw materials are all simple and easy to obtain, security and stability of the compound, the reaction time is short, after the reaction by simple extraction, concentration or crystallization can be obtained pure product, at the same time can also be realized in the use of the recycling of the catalyst, catalyst recycled is very convenient and almost no "wastes" problem. The invention it has less catalyst levels, the reaction selectivity is high, and the yield is high, the operation is simple, pollution is small, green high degree of several advantages; in the setting under the reaction conditions, the conversion of raw materials and the yield of the product are as high as 90% or more. (by machine translation)

Dinuclear manganese alkoxide complexes as catalysts for C-N bond cleavage of simple tertiary: N, N -dialkylamides to give esters

Amide bonds are stable due to the resonance between the nitrogen lone pair and the carbonyl moiety, and therefore the chemical transformation of amides, especially tertiary amides, involving C-N bond fission is considered one of the most difficult organic reactions, unavoidably requiring harsh reaction conditions and strong acids or bases. We report the catalytic C-N bond cleavage of simple tertiary N,N-dialkylamides to give corresponding esters using a catalyst system (2 mol% based on Mn atoms) of a tetranuclear manganese alkoxide, [Mn(acac)(OEt)(EtOH)]4 (1c), combined with four equivalents of 4,7-bis(dimethylamino)-1,10-phenanthroline (L1: Me2N-Phen). Regarding the reaction mechanism, we isolated a dinuclear manganese complex, [Mn(acac)(OEt)(Phen)]2 (6c), which was revealed as the catalytically active species for the esterification of tertiary amides.