128592-61-0Relevant academic research and scientific papers
Predicting hydration propensities of biologically relevant α-ketoamides
Wedler, Henry B.,Palazzo, Teresa A.,Pemberton, Ryan P.,Hamann, Christian S.,Kurth, Mark J.,Tantillo, Dean J.
, p. 4153 - 4157 (2015)
Quantum chemical calculations coupled to experiments were used to predict covalent hydration propensities of biologically relevant α-ketoamides. Experimentally determined hydration equilibrium constants for related ketones and aldehydes were compared to c
C-H/C-C Functionalization Approach to N-Fused Heterocycles from Saturated Azacycles
Ham, Jin Su,Park, Bohyun,Son, Mina,Roque, Jose B.,Jurczyk, Justin,Yeung, Charles S.,Baik, Mu-Hyun,Sarpong, Richmond
supporting information, p. 13041 - 13050 (2020/09/01)
Herein we report the synthesis of substituted indolizidines and related N-fused bicycles from simple saturated cyclic amines through sequential C-H and C-C bond functionalizations. Inspired by the Norrish-Yang Type II reaction, C-H functionalization of azacycles is achieved by forming α-hydroxy-β-lactams from precursor α-ketoamide derivatives under mild, visible light conditions. Selective cleavage of the distal C(sp2)-C(sp3) bond in α-hydroxy-β-lactams using a Rh-complex leads to α-acyl intermediates which undergo sequential Rh-catalyzed decarbonylation, 1,4-addition to an electrophile, and aldol cyclization, to afford N-fused bicycles including indolizidines. Computational studies provide mechanistic insight into the observed positional selectivity of C-C cleavage, which depends strongly on the groups bound to Rh trans to the phosphine ligand.
Cu-Catalyzed aerobic oxidative cleavage of C(sp3)–C(sp3) bond: Synthesis of α-ketoamides
Fang, Zheng,Guo, Kai,Liu, Chengkou,Yang, Man,Zhang, Jingming
supporting information, (2020/11/02)
A novel synthesis of α-ketoamides from Cu-catalyzed aerobic oxidative C(sp3)–C(sp3) bond cleavage of hydrocinnamaldehydes has been developed. Readily available and environmentally benign oxygen is used as the oxidant. This reaction avoids the use of noble metal catalysts or specialized oxidants, and chemoselectively yields α-ketoamide. Moreover, based on various control experiments, a reasonable mechanism is proposed.
POP-Pd(ii) catalyzed easy and safe: In situ carbonylation towards the synthesis of α-ketoamides from secondary cyclic amines utilizing CHCl3 as a carbon monoxide surrogate
Islam, Sk Safikul,Riyajuddin, Sk,Molla, Rostam Ali,Yasmin, Nasima,Ghosh, Kaushik,Islam, Sk. Manirul
, p. 1979 - 1987 (2020/02/13)
A novel complex catalyst, POP-palladium(ii), has been synthesized. The developed catalyst has been characterized by XRD, EDX, scanning electron microscopy (FE-SEM), HR-TEM, FTIR spectroscopy, UV-vis spectroscopy, TGA and BET isotherm analysis. The reactiv
Stabilized Cu2O nanoparticles on rGO highly catalyzed direct oxidative coupling synthesis of Α-ketoamides with molecular oxygen
Lu, Weiyang,Sun, Wei,Tan, Xiaofeng,Wang, Bin,Yang, Hua,Gao, Lingfeng,Zheng, Gengxiu
, (2019/09/10)
In this study, a green, efficient, recyclable Cu2O nanoparticles on reduced graphene oxide (Cu2O-NPs@rGO) carbon-based composite catalyst was synthesized by facile one-pot hydrothermal method. And Cu2O-NPs@rGO catalyst was
Polymer supported triazine based palladium complex catalyzed double carbonylation reaction of halo aryl compounds for the synthesis of α-ketoamides
Islam, Sk Safikul,Molla, Rostam Ali,Ta, Sabyasachi,Yasmin, Nasima,Das, Debasis,Islam, Sk Manirul
, p. 18 - 25 (2019/01/08)
Novel polystyrene incorporated Palladium (II) catalyst was developed and well characterized. The efficiency of the supported Pd(II) catalytic material was checked for double carbonylation reaction of 2° amines and aryl iodides to their corresponding α-ketoamides under high pressure reaction conditions. The reaction was carried out in 60 psi carbon monoxide pressure. An extensive variety of aryl iodides in combination with 2° amines in presence of carbon monoxide can produce the respective α-ketoamides with superb chemoselectivity. Effect of solvents, bases, time and amount of catalyst for the production of α-ketoamides were reported. This supported Pd(II)complex was highly catalytically active and recyclable. The developed catalytic material was regenerated by filtration. It could be recycled further six times with no such profound loss in its activity.
UV Assisted High-Efficient Synthesis of α-Ketoamides using Air Promoted by A Non-Metal Catalyst in Aqueous Solution
Li, Jianhui,He, Shaopo,Zhang, Kuan,Quan, Ziyi,Shan, Qiheng,Sun, Zhongliang,Wang, Bo
, p. 4868 - 4873 (2018/10/15)
Presented here is the first example of UV (λ=210 nm) promoted procedure proceeding in aqueous media at room temperature using ambient air as the oxidant for efficient synthesis of an array of α-ketoamides of all types using a non-metal catalyst N-iodosuccinimide with a loading of 20 mol%. With UV, oxygen in the air was efficiently utilized as the green oxidant, some control experiments were carried out and a plausible mechanism was proposed, disclosing that in aqueous solution, the oxidation process was actually triggered by dioxygen radical anion (O2.?), while not molecular oxygen. A variety of secondary amines and primary amines as well as ammonia were employed as the amine moieties, and the desired product primary-, secondary-, and tertiary α-ketoamides were afforded in good to excellent yields of up to 96 %.
Aerobic oxidative amidation of alkynes using titanium oxide encapsulated cuprous iodide nanoparticles (CuI@TiO2)
Dutta, Pratip Kumar,Dhar, Basabbijayi,Sen, Subhabrata
, p. 12062 - 12071 (2018/07/24)
A catalyst consisting of titanium oxide encapsulated cuprous iodide nanoparticles was prepared via a sol-gel method using inexpensive raw materials and was harnessed successfully in the oxidative amidation of alkynes via an environmentally benign and sustainable protocol. The mechanism of action of this transformation was thoroughly discussed. The robustness of the catalyst was elucidated by the synthesis of diverse analogues of α-ketoarylamide from a variety of electron rich and poor substrates via a simple procedure in moderate to high yields, with no generation of toxic by-products, in good recyclability up to five cycles, under solvent free and aerobic conditions. The chemical nature, morphology and loading of the CuI@TiO2 nanocatalyst were investigated by TEM, SEM, XPS, EDX, powder XRD, BET, TGA and ICP-MS.
Versatile Heterogeneous Palladium Catalysts for Diverse Carbonylation Reactions under Atmospheric Carbon Monoxide Pressure
Vico Solano, Marta,González Miera, Greco,Pascanu, Vlad,Inge, A. Ken,Martín-Matute, Belén
, p. 1089 - 1095 (2018/02/06)
Herein, we report a versatile carbonylation protocol using heterogeneous Pd0 nanoparticles supported on the metal–organic frameworks (MOFs) MIL-88B-NH2 (Fe/Cr). The synthesis of a vast array of carbonyls, which includes amides, esters, carboxylic acids, and α-ketoamides, was achieved through mono- and dicarbonylation reactions. The selectivity could be controlled simply by tuning the reaction conditions. Superior activity and selectivity were recorded in some cases compared to that achieved with commercial Pd/C. However, the utility of an elaborate catalyst support is questionable and important reactivity and recyclability issues are discussed.
Water dispersed gold nanoparticles catalyzed aerobic oxidative cross-dehydrogenative coupling: An efficient synthesis of α-ketoamides in water
Thirukovela, Narasimha Swamy,Balaboina, Ramesh,Vadde, Ravinder,Sekhar Vasam, Chandra
supporting information, p. 3749 - 3752 (2018/09/17)
An effective green synthesis of α-ketoamides was developed for the first time in water via gold nanoparticles (AuNPs) catalyzed aerobic oxidative cross-dehydrogenative coupling of secondary amines with phenylglyoxals with a broad substrate scope.
