22867-46-5Relevant academic research and scientific papers
Ynamide-Mediated Intermolecular Esterification
Wang, Xuewei,Yang, Yang,Zhao, Yongli,Wang, Sheng,Hu, Wenchang,Li, Jinmei,Wang, Zihao,Yang, Fengling,Zhao, Junfeng
, p. 6188 - 6194 (2020/05/26)
An ynamide-mediated one-pot, two-step intermolecular esterification via the condensation of carboxylic acids with nucleophilic hydroxyl species was reported. A broad substrate scope with respect to carboxylic acids, alcohols, and phenols was observed. The α-acyloxyenamide intermediates formed by the addition of carboxylic acids to ynamides proved to be effective acylating reagents for the esterification of alcohol and phenol derivatives with the assistance of base catalysis. Notably, the racemization of the α-chiral center of carboxylic acids can be avoided.
Exploring the influence of designer surfactant hydrophobicity in key C–C/C–N bond forming reactions
Reddy, Singarajanahalli Mundarinti Krishna,Kothandapani, Jagatheeswaran,Sengan, Megarajan,Veerappan, Anbazhagan,Selva Ganesan, Subramaniapillai
, p. 80 - 86 (2019/01/14)
Designer micellar medium was explored for the transformation of diverse anilines to the corresponding densely substituted biologically relevant skatole derivatives in an aqueous medium via 5-exo-trig cyclization reaction. The scope of the reaction was extended to intermolecular Csp2-Csp2 and Csp2-N bond forming reactions in water. Systematic investigations revealed that altering hydrophobicity of surfactant influences the yield of both C–C and C–N bond forming reactions in water.
A novel aromatic carbocation-based coupling reagent for esterification and amidation reactions
Nguyen, Thanh V.,Lyons, Demelza J.M.
supporting information, p. 3131 - 3134 (2015/06/17)
A novel tropylium-based coupling reagent has been developed to facilitate the synthesis of a series of esters, amides, lactones and peptides under mild reaction conditions. Remarkably, this reagent can be used in catalytic amounts in conjunction with a sacrificial reagent, offering a new and efficient method for nucleophilic coupling reactions of carboxylic acids.
Influence of electronically and sterically tunable cinnamate ligands on the spectroscopic, kinetic, and thermodynamic properties of bis(triphenylphosphine) palladium(0) olefin complexes
Buchner, Magnus R.,Bechlars, Bettina,Wahl, Bernhard,Ruhland, Klaus
experimental part, p. 588 - 601 (2012/03/22)
A detailed study of the influence of electronic and steric characteristics of cinnamic acid esters on the spectroscopic, kinetic, and thermodynamic properties of bis(triphenylphosphine)palladium(0) cinnamic acid ester complexes is presented (51 different new complexes included). These complexes show a dynamic behavior on the NMR spectroscopic time scale. Therefore, the rotational barriers of the olefin about the metalolefin bond as well as the dissociation entropy and enthalpy of the olefin and the dissociation mechanism could be determined. These findings are interpreted together with the NMR spectroscopic, IR spectroscopic, and X-ray structural data (7 new structures included) concerning the influence of the different olefin ligands on the complex properties by means of Hammett plots. DFT calculations were performed to support the mechanistic conclusions.
TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes: A novel method for the solid-phase synthesis of dihydrocoumarins and coumarins
Tang,Li, Wen,Gao, Zhang Yong,Gu, Xi
body text, p. 631 - 634 (2012/07/03)
TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes was performed using polystyrene-supported succinimidyl selenide as the selenium source. This catalytic process provides an efficient method for the regioselective synthesis of dihydrocoumarins possessing a seleno-functionality, followed by traceless cleavage of selenium linker to provide dihydrocoumarins and coumarins in good yields and purities.
NHC-catalyzed C-O or C-N bond formation: Efficient approaches to α,β-unsaturated esters and amides
Zhang, Bo,Feng, Peng,Cui, Yuxin,Jiao, Ning
supporting information; experimental part, p. 7280 - 7282 (2012/07/28)
Simple and efficient NHC-catalyzed transformations of bromoenal or α,β-dibromoenal into α,β-unsaturated esters or amides with high stereoselectivity through C-O or C-N bond formation have been demonstrated. The NHC-catalyzed processes occur under mild con
Selective synthesis of 3,4-dihydrocoumarins and chalcones from substituted aryl cinnamic esters
Jeon, Jae-Ho,Yang, Deok-Mo,Jun, Jong-Gab
experimental part, p. 65 - 70 (2011/10/31)
Coumarins are ubiquitous in plant kingdom and have been used as antitumor, antifungals, anticoagulants, insecticides. Chalcones are also widespread in plant kingdom and have been known to possess diverse biological activities; antibacterial, antifungal, antitumor and anti-inflammatory, etc. As they are considered as important natural products, numerous synthetic approaches have been reported up to the present. We devise a new selective method of preparing dihydrocoumarins and chalcones from aryl cinnamates by the selection of reagents. Dihydrocoumarin derivatives were prepared selectively by using intramolecular cyclization catalyzed by p-toluene sulfonic acid. Also, chalcones were prepared by Fries-rearrangement catalyzed by TiCl4. This method can be used for preparing various coumarin & chalcone compounds.
Conjugate addition of lithium N -phenyl- N -(α-methylbenzyl)amide: Application to the asymmetric synthesis of (R)-(-)-angustureine
Bentley, Scott A.,Davies, Stephen G.,Lee, James A.,Roberts, Paul M.,Thomson, James E.
supporting information; experimental part, p. 2544 - 2547 (2011/06/25)
The conjugate addition of lithium (R)-N-phenyl-N-(α-methylbenzyl) amide to a range of α,β-unsaturated 4-methoxyphenyl esters proceeds with excellent levels of diastereoselectivity to give the corresponding β-amino esters in good yield and as single diaste
Preyssler catalyst: An efficient catalyst for esterification of cinnamic acids with phenols and imidoalcohols
Ruiz, Diego M.,Romanelli, Gustavo P.,Vázquez, Patricia G.,Autino, Juan C.
experimental part, p. 110 - 119 (2010/11/04)
In the present work a series of eco-friendly Preyssler solid acids and their salts H14[NaP5W29MoO110] (PW), H14[NaP5W30O110] (PWMo), K12.5Na1.5[NaP5W30O110]·15H2O (PWK), K12.5Na1.5[NaP5W29MoO110]·15H2O (PWMoK) and 10% silica-supported H14[NaP5W29MoO110] (PWSiO2), and H14[NaP5W30O110] (PWMoSiO2) have been used as catalysts for the direct esterification of cinnamic acids with phenols or 2-(N-phthalimidoethanol). Effects of the reaction conditions were studied, including temperature, reaction time, and type and amount of catalyst. These solids were characterized by several techniques, such as diffuse reflectance spectroscopy, Fourier transformed infrared spectroscopy, optical and scanning electron microcopies, and X-ray diffraction, among others. The most adequate catalyst for performing the title reaction was H14[NaP5W30O110] (PWMo). The catalyst was applied for the synthesis of various substituted cinnamates, giving very good yields.
Ru(III)-Catalyzed Cyclization of Arene-Alkene Substrates via Intramolecular Electrophilic Hydroarylation
Youn, So Won,Pastine, Stefan J.,Sames, Dalibor
, p. 581 - 584 (2007/10/03)
(Matrix presented) We herein report that RuCl3/AgOTf has proven to be a hydroarylation catalyst with an efficiency and scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-ene substrates of diverse structural features, providing good to excellent yields of cyclization products (chromanes, tetralins, terpenoids, dihydrocoumarins).
