2451-86-7Relevant academic research and scientific papers
Solvent-free synthesis of symmetric methylene diestersviadirect reaction of aromatic carboxylates with 1,n-dihaloalkanes
Bai, Lin,Ding, Shenglong,Ma, Xiaofang
, p. 28711 - 28715 (2021/09/22)
An efficient methodology for the synthesis of symmetrical methylene diesters was developed through direct reaction of various aromatic carboxylates with 1,n-dihaloalkanes under solvent-free conditions. This strategy offers a high product yield, facile work-up and purification, and an environmentally friendly approach to obtain long-chain methylene carboxylate scaffolds with increased diversity.
Hydrogen-bond-assisted transition-metal-free catalytic transformation of amides to esters
Huang, Changyu,Li, Jinpeng,Wang, Jiaquan,Zheng, Qingshu,Li, Zhenhua,Tu, Tao
, p. 66 - 71 (2020/11/18)
The amide C-N cleavage has drawn a broad interest in synthetic chemistry, biological process and pharmaceutical industry. Transition-metal, luxury ligand or excess base were always vital to the transformation. Here, we developed a transition-metal-free hydrogen-bond-assisted esterification of amides with only catalytic amount of base. The proposed crucial role of hydrogen bonding for assisting esterification was supported by control experiments, density functional theory (DFT) calculations and kinetic studies. Besides broad substrate scopes and excellent functional groups tolerance, this base-catalyzed protocol complements the conventional transition-metal-catalyzed esterification of amides and provides a new pathway to catalytic cleavage of amide C-N bonds for organic synthesis and pharmaceutical industry. [Figure not available: see fulltext.]
Direct conversion of aromatic 1,3-dioxanes to hydroxypropyl esters with pyridinium hydrobromide perbromide and sodium acetate in water
Sayama, Shinsei
, p. 859 - 864 (2017/06/13)
Various aromatic 1,3-dioxanes were directly converted to respective hydorxypropyl esters with pyridinum hydrobromide perbromide and sodium acetate in water at room temperature.
Nanoscaled inclusion complexes of β-cyclodextrin with binuclear compounds based on diols containing fragments of selected aromatic monocarboxylic acids
Kurochkina,Grachev,Batalova
, p. 753 - 757 (2014/06/09)
Stable nanoscaled mono- and dimeric inclusion complexes of β-cyclodextrin with hosts based on symmetric diols of various length containing fragments of benzoic, nicotinic, or isonicotinic acid were synthesized.
Facile esterification of carboxylic acid using amide functionalized benzimidazolium dicationic ionic liquids
Muskawar, Prashant Narayan,Thenmozhi,Gajbhiye, Jayant M.,Bhagat, Pundlik Rambhau
, p. 214 - 220 (2014/07/08)
Herein, we report the synthesis of a new series of amide functionalized dicationic benzimidazolium based ionic liquids (DBimILs) and appraised their efficacy towards perceptive esterification of carboxylic acids with alkyl/allyl/aryl halides in presence of triethylamine. The amide groups present in this new series of DBimILs are expected to form hydrogen bonding with the carboxylic acids and this could facilitate the esterification reactions under mild conditions devoid of any added catalyst or organic solvent. The plausible mechanism for the enhanced catalytic activity in presence of this new series of ILs has been proposed. The corresponding alkyl/allyl/aryl esters isolated from this reaction were of high purity after simple extraction, which wipe out the necessity for further purification. This protocol addresses clean methodology and the efficient recyclability as well as reusability of the catalyst.
Odd-even effect of dopant molecules on clearing temperatures of nematic liquid-crystal phases
Kishikawa, Keiki,Haga, Yuri,Inoue, Takahiro,Watanabe, Tomohiro,Takahashi, Masahiro,Kohmoto, Shigeo
supporting information, p. 1465 - 1467 (2013/01/16)
Nematic liquid-crystal phases doped with the novel dopant compounds 1 (C6F5COO(CH)nOCOC6F5, n = 17) and 2 (C6H5-COO(CH)nOCOC6H 5, n = 17) showed an "opposite odd-even effect" on clearing temperatures. The tendency was exactly opposite to that reported for liquid-crystal dimers. A mechanism is postulated on the basis of the difference in the formation of molecular aggregations of even- and odd-number-dopant molecules in the host liquid-crystal molecules.
Imidazol(in)ium-2-carboxylates as latent, thermally activated organocatalysts for transesterification reactions
Wang, Yanqin,Li, Zhenjiang
experimental part, p. 502 - 507 (2012/07/17)
1,3-Disubstituted imidazol(in)ium-2-carboxylates (ImCO2) were used as precatalysts for transesterification reactions of unactivated ethyl benzoate with monohydric alcohols, dihydric alcohols, and amino alcohols. Highly active N-heterocyclic carbenes (NHCs) are usually not used directly as catalysts because of their air and moisture sensitivity. Here they were liberated in situ by thermal decarboxylation of ImCO2 at designated temperatures. The results showed that the yield of the reactions reached up to 95 within 3 h using only 0.5 mol catalyst. No active enol esters, molecular sieves, or a 20-fold excess of alcohol were used to drive the reaction to completion. It was proved that unsaturated imidazolium-2-carboxylates have a better activity than saturated species in this type of reaction. Different types of substituting groups of ImCO2 exhibited varied transesterification activity.
Imidazol(in)ium-2-carboxylates as Latent, Thermally Activated Organocatalysts for Transesterification Reactions
Wang, Yanqin,Li, Zhenjiang
, p. 502 - 507 (2016/04/10)
1,3-Disubstituted imidazol(in)ium-2-carboxylates (ImCO2) were used as precatalysts for transesterification reactions of unactivated ethyl benzoate with monohydric alcohols, dihydric alcohols, and amino alcohols. Highly active N-heterocyclic carbenes (NHCs) are usually not used directly as catalysts because of their air and moisture sensitivity. Here they were liberated in situ by thermal decarboxylation of ImCO2 at designated temperatures. The results showed that the yield of the reactions reached up to 95% within 3 h using only 0.5 mol% catalyst. No active enol esters, molecular sieves, or a 20-fold excess of alcohol were used to drive the reaction to completion. It was proved that unsaturated imidazolium-2-carboxylates have a better activity than saturated species in this type of reaction. Different types of substituting groups of ImCO2 exhibited varied transesterification activity.
Molybdenum hexacarbonyl mediated alkoxycarbonylation of aryl halides
Ren, Wei,Emi,Yamane, Motoki
experimental part, p. 2303 - 2309 (2011/09/19)
Mo(CO)mediates the alkoxycarbonylation of aryl halides in their reaction with alcohols to afford arenecarboxylic acid esters. The molybdenum carbonyl complexes act as the catalyst and the source with carbon monoxide. The alkoxycarbonylation proceeds with a small excess of carbon monoxide in the form of Mo(CO)and the procedure is simple compared to the conventional method, which uses palladium catalyst under gaseous carbon monoxide. Using this procedure, a variety of carboxylic acid esters were prepared. Georg Thieme Verlag Stuttgart ? New York.
Inclusion compound of β-cyclodextrin with binuclear guests containing residues of some pharmocologically important aromatic monocarboxylic acids
Grachev,Charaev,Kurochkina,Batalova,Soboleva,Vasyanina,Nifant'ev
experimental part, p. 2129 - 2135 (2012/03/12)
Stable monomeric and dimeric inclusion compounds of β-cyclodextrin with binuclear guests containing the residues of some pharmacologically important aromatic monocarboxylic acids were obtained. Pleiades Publishing, Ltd., 2011.
