57409-40-2Relevant academic research and scientific papers
Visible-Light-Mediated Oxidative Amidation of Aldehydes by Using Magnetic CdS Quantum Dots as a Photocatalyst
Xu, Ling,Zhang, Shuai-Zheng,Li, Wei,Zhang, Zhan-Hui
, p. 5483 - 5491 (2021/03/01)
A magnetic CdS quantum dot (Fe3O4/polydopamine (PDA)/CdS) was synthesized through a facile and convenient method from inexpensive starting materials. Characterization of the prepared catalyst was performed by means of FTIR spectrosco
Synthesis and characterization of bridged bis(amidato) rare earth metal amides and their applications in C-N bond formation reactions
Zhao, Bei,Xiao, Yang,Yuan, Dan,Lu, Chengrong,Yao, Yingming
, p. 3880 - 3887 (2016/03/05)
Based on three bisamide proligands H2Ln (n = 1-3) (H2L1 = [(Me3C6H2CONHCH2)2CH2], H2L2 = [(Me3C6H2CONHCH2)2C(CH3)2], H2L3 = [Me3C6H2CONH(CH2)2]2NCH3), eight bis(amidato) trivalent rare-earth metal amides {LnRE[N(TMS)2]}2 (n = 1, RE = La (1), Sm (2), Nd (3), Y (4); n = 2, RE = La (5), Nd (6); n = 3, RE = La (7), Nd (8); TMS = SiMe3) were successfully synthesized by treatment of H2Ln with RE[N(TMS)2]3 in a 1:1 molar ratio. Complexes 3, and 5-8 were characterized by single-crystal X-ray diffraction, and NMR characterization was carried out for the La complexes 1, 5, 7 and the Y complex 4. These complexes exhibited high catalytic activities in both the direct amidation of aldehydes and the addition of amines with carbodiimine. It was found that the bis(amidato) rare earth metal amides bearing different linkers have different effects on the transformations and lanthanum and neodymium complexes performed better than others.
Dioxygen-promoted Pd-catalyzed aminocarbonylation of organoboronic acids with amines and CO: A direct approach to tertiary amides
Ren, Long,Li, Xinwei,Jiao, Ning
supporting information, p. 5852 - 5855 (2016/11/29)
A direct approach from organoboronic acids and amines to tertiary amides via Pd-catalyzed aerobic aminocarbonylation has been developed. The presence of O2 significantly promotes the efficiency of this transformation. This method uses commercially available organoboronic acids and cheap CO and O2 (1 atm), which renders amides an easy synthesis with broad substrate scope and high functional group tolerance.
Anionic phenoxy-amido rare-earth complexes as efficient catalysts for amidation of aldehydes with amines
Wang, Chao,Huang, Lingling,Lu, Min,Zhao, Bei,Wang, Yaorong,Zhang, Yong,Shen, Qi,Yao, Yingming
, p. 94768 - 94775 (2015/11/24)
A series of anionic organo-rare-earth amido complexes stabilized by dianionic phenoxy-amido ligands were prepared and their catalytic behavior for amidation reactions of aldehydes with amines was elucidated. Amine elimination reaction of Ln[N(SiMe3)2]3(μ-Cl)Li(THF)3 with an equimolar of lithium aminophenoxy {[HNO]1Li(THF)}2, which was prepared by the reaction of [HNOH]1 {[HNOH]1 = N-p-fluoro-phenyl(2-hydroxy-3,5-di-tert-butyl)benzylamine} with one equivalent of n-BuLi in tetrahydrofuran (THF) in situ, gave the anionic phenoxy-amido rare earth amido complexes [NO]12Ln[N(SiMe3)2][Li(THF)]2 [Ln = Y (1), Yb (2), Sm (3), Nd (4)] in high isolated yields. Similar reactions of Ln[N(SiMe3)2]3(μ-Cl)Li(THF)3 with {[HNO]2Li(THF)}2, and {[HNO]3Li(THF)}2 in THF gave the anionic rare-earth amides [NO]22Ln[N(SiMe3)2][Li(THF)]2 [Ln = Sm (5), Nd (6)] and [NO]32Ln[N(SiMe3)2][Li(THF)]2 [Ln = Sm (7), Nd (8)] {[HNOH]2 = N-p-chloro-phenyl(2-hydroxy-3,5-di-tert-butyl)benzylamine; [HNOH]3 = N-p-bromo-phenyl(2-hydroxy-3,5-di-tert-butyl)benzylamine}, respectively. All of these complexes were fully characterized. X-ray structural determination revealed that these complexes are isostructural, and have solvated monomeric structures. Each of the rare-earth ions is coordinated by two phenoxy-amido ligands and one N(SiMe3)2 group, and the coordination geometry can be described as a distorted trigonal bipyramid. Each of the lithium atoms is surrounded by one aryloxo group, one amido group and one THF molecule, and the coordination geometry can be described as a trigonal plane. The catalytic behavior of these rare-earth amides for the amidation reaction of aldehyde with amine was elucidated. It was found that these complexes are efficient catalysts for this transformation to produce amides in good to excellent yields under mild reaction conditions, and in some cases, diacylamide compounds can be prepared conveniently.
Direct amidation from alcohols and amines through a tandem oxidation process catalyzed by heterogeneous-polymer-incarcerated gold nanoparticles under aerobic conditions
Soule, Jean-Francois,Miyamura, Hiroyuki,Kobayashi, Shu
supporting information, p. 2614 - 2626 (2013/11/19)
We describe herein a highly elegant and suitable synthesis of amide products from alcohols and amines through a tandem oxidation process that uses molecular oxygen as a terminal oxidant. Carbon-black-stabilized polymer-incarcerated gold (PICB-Au) or gold/cobalt (PICB-Au/Co) nanoparticles were employed as an efficient heterogeneous catalyst depending on alcohol reactivity and generated only water as the major co-product of the reaction. A wide scope of substrate applicability was shown with 42 examples. The catalysts could be recovered and reused without loss of activity by using a simple operation. Gold standard: A highly efficient green method for amide synthesis from alcohols and amines catalyzed by gold nanoparticles stabilized by styrene-based copolymers has been developed (see scheme). Two catalysts have been used with high selectivity depending on the combination of substrates. These Au nanoparticle catalysts can be recovered and reused several times by simple operations. Copyright
Atmospheric pressure aminocarbonylation of aryl iodides using palladium nanoparticles supported on MOF-5
Dang, Tuan T.,Zhu, Yinghuai,Ghosh, Subhash C.,Chen, Anqi,Chai, Christina L. L.,Seayad, Abdul M.
supporting information; experimental part, p. 1805 - 1807 (2012/03/08)
An efficient amide synthesis by atmospheric pressure aminocarbonylation using palladium nanoparticles supported on MOF-5 is reported. Interestingly, only 0.5 wt% palladium loading was required to achieve high yields. The catalyst is recyclable and offers negligible palladium leaching.
Synthesis and structural diversity of heterobimetallic lanthanide-potassium complexes and catalytic activity for amidation of aldehydes with amines
Xu, Bin,Huang, Lingling,Yang, Zijian,Yao, Yingming,Zhang, Yong,Shen, Qi
experimental part, p. 3588 - 3595 (2011/09/12)
Four heterobimetallic lanthanide-potassium complexes stabilized by the carbon-bridged bis(phenolate) ligand MBMP2- (MBMP = 2,2′-methylene bis(6-tert-butyl-4-methylphenolate)), [{(MBMP) 2La(THF)2}2K][K(THF)6] (1), [(MBMP)Nd(μ-MBMP)K(THF)]2 (2), [(THF)2Sm(MBMP) 2K(THF)2] (3), and [(THF)2Yb(MBMP) 2K(THF)3] (4), were synthesized, and their structural features were provided. It was found that the ionic radii of lanthanide metals have a profound effect on the structures of the heterobimetallic complexes. Complexes 1 to 4 are efficient catalysts for amidation reactions of aldehydes with amines to produce amides in good to excellent yields under mild conditions.
Powerful amide synthesis from alcohols and amines under aerobic conditions catalyzed by gold or gold/iron, -nickel or-cobalt nanoparticles
Soule, Jean-Francois,Miyamura, Hiroyuki,Kobayashi, Shu
experimental part, p. 18550 - 18553 (2012/01/06)
Considering the importance of the development of powerful green catalysts and the omnipresence of amide bonds in natural and synthetic compounds, we report here on reactions between alcohols and amines for amide bond formation in which heterogeneous gold and gold/iron, -nickel, or-cobalt nanoparticles are used as catalysts and molecular oxygen is used as terminal oxidant. Two catalysts show excellent activity and selectivity, depending on the type of alcohols used. A wide variety of alcohols and amines, including aqueous ammonia and amino acids, can be used for the amide synthesis. Furthermore, the catalysts can be recovered and reused several times without loss of activity.
Catalytic transamidation reactions compatible with tertiary amide metathesis under ambient conditions
Stephenson, Nickeisha A.,Zhu, Jiang,Gellman, Samuel H.,Stahl, Shannon S.
experimental part, p. 10003 - 10008 (2009/12/08)
The carbon-nitrogen bond of carboxamides is extremely stable under most conditions. The present study reveals that simple zirconium- and hafnium-amido complexes are highly efficient catalysts for equilibrium-controlled transamidation reactions between sec
Discovery and mechanistic study of AlIII-catalyzed transamidation of tertiary amides
Hoerter, Justin M.,Otte, Karin M.,Gellman, Samuel H.,Cui, Qiang,Stahl, Shannon S.
, p. 647 - 654 (2008/10/09)
Cleavage of the C-N bond of carboxamides generally requires harsh conditions. This study reveals that tris(amido)AlIII catalysts, such as Al2(NMe2)6, promote facile equilibrium-controlled transamidation of tertiary carboxamides with secondary amines. The mechanism of these reactions was investigated by kinetic, spectroscopic, and density functional theory (DFT) computational methods. The catalyst resting state consists of an equilibrium mixture of a tris(amido)AlIII dimer and a monomeric tris(amido)Al III-carboxamide adduct, and the turnover-limiting step involves intramolecular nucleophilic attack of an amido ligand on the coordinated carboxamide or subsequent rearrangement (intramolecular ligand substitution) of the tetrahedral intermediate. Fundamental mechanistic differences between these tertiary transamidation reactions and previously characterized transamidations involving secondary amides and primary amines suggest that tertiary amide/secondary amine systems are particularly promising for future development of metal-catalyzed amide metathesis reactions that proceed via transamidation.
