899663-73-1Relevant academic research and scientific papers
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.]
Base-Promoted Amidation and Esterification of Imidazolium Salts via Acyl C-C bond Cleavage: Access to Aromatic Amides and Esters
Karthik, Shanmugam,Muthuvel, Karthick,Gandhi, Thirumanavelan
, p. 738 - 751 (2019/01/24)
Imidazolium salts have been effectively employed as suitable acyl transfer agents in amidation and esterification in organic synthesis. The weak acyl C(O)-C imidazolium bond was exploited to generate acyl electrophiles, which further react with amines and alcohols to afford amides and esters. The broad substrate scope of anilines and benzylic amines and base-promoted conditions are the benefits of this route. Interestingly, phenol, benzylic alcohols, and a biologically active alcohol can also be subjected to esterification under the optimized conditions.
Copper catalyzed oxidative esterification of aldehydes with alkylbenzenes via cross dehydrogenative coupling
Rout, Saroj Kumar,Guin, Srimanta,Ghara, Krishna Kanta,Banerjee, Arghya,Patel, Bhisma K.
supporting information; experimental part, p. 3982 - 3985 (2012/09/22)
Copper(II) as the catalyst in a cross dehydrogenative coupling (CDC) reaction has been demonstrated for the synthesis of benzylic esters using aldehydes and alkylbenzenes as coupling partners.
Chlorobenzyl alcohols from chlorobenzyl chlorides via corresponding benzoate esters: Process development aspects
Joshi,Sawant
, p. 23 - 29 (2013/09/07)
Kinetic studies in conversion of benzyl chlorides to corresponding alcohols via the benzoates are presented in this paper. The esterification reaction of 2-chlorobenzyl chloride, 4-chlorobenzyl chloride, 2,4-dichlorobenzyl chloride and benzyl chloride with aqueous sodium benzoate in the presence of phase transfer catalysts was investigated. The parameters studied are stirring speed, catalysts, the catalyst loading, temperature and the concentration of aqueous phase. The esterification reaction follows pseudo-first-order kinetics. The esters, were hydrolysed with and without a phase transfer catalyst to give corresponding benzyl alcohols without involving respective dibenzyl ethers. Material balance for the laboratory batch process of each chlorobenzyl alcohol has also been presented. A recycle strategy presented is shown to be effective in terms of alkali and benzoic acid consumption as the reactants are consumed to near stoichiometric levels.
