122-98-5Relevant articles and documents
Copper-catalyzed C-N cross-coupling reactions for the preparation of aryl diamines applying mild conditions
Costa, Márcio V.,Viana, Gil M.,De Souza, Thaís M.,Malta, Luiz Fernando B.,Aguiar, Lúcia C.S.
, p. 2332 - 2335 (2013)
In this work, aryl diamines were prepared by C-N cross-coupling reactions between aryl halides and ethylenediamine. These reactions were successfully catalyzed by low quantities of Cu2O or CuO (1 mol %) employing low reflux temperature and low diamine excess. Products were afforded in good yields (up to 95%).
An efficient synthesis of organic carbonates using nanocrystalline magnesium oxide
Kantam, M. Lakshmi,Pal, Ujjwal,Sreedhar,Choudary
, p. 1671 - 1675 (2007)
An efficient and selective synthesis of organic carbonates using nanocrystalline magnesium oxide has been realized by the direct condensation of alcohols and diethyl carbonate. The catalyst is quantitatively recovered by simple centrifugation and can be reused for four cycles with almost consistent activity.
BmimOAc ionic liquid: A highly efficient catalyst for synthesis of 3-aryl-2-oxazolidinones by direct condensation of 2-(arylamino) alcohols with diethyl carbonate
Elageed, Elnazeer H.M.,Wang, Binshen,Zhang, Yongya,Wu, Shi,Gao, Guohua
, p. 271 - 277 (2015)
An efficient convenient procedure for the synthesis of 3-aryl-2-oxazolidinones from 2-(arylamino) alcohols and diethyl carbonate (DEC) catalyzed by ionic liquids is described. The effects of reaction time, amount of catalyst and temperature were investigated. Excellent yields of products were obtained under the optimized reaction conditions, when using BmimOAc as a catalyst. An intermediate ethyl 2-(phenyl amino) ethyl carbonate was isolated and characterized. 1H NMR spectroscopy and DFT calculations indicated that BmimOAc cooperatively activate the substrates through hydrogen bonding with its anion and cation sites. According to these results, a possible reaction mechanism was discussed.
An efficient and recyclable chitosan supported copper(II) heterogeneous catalyst for C-N cross coupling between aryl halides and aliphatic diamines
Bodhak, Chandan,Kundu, Ashis,Pramanik, Animesh
, p. 419 - 424 (2015)
A useful and convenient methodology has been developed for synthesis of mono N-arylated aliphatic 1,2- and 1,3-diamines and amino alcohols. A highly efficient and renewable heterogeneous chitosan supported copper(II) catalyst has been employed for the C-N cross coupling between aryl halides and aliphatic diamines/amino alcohols. The main advantages of this reaction are the high yields of the products, reduced reaction time, convenient work up procedure, renewability of the catalyst, and less metal contamination of the products. All these factors make the present C-N cross coupling reaction economical, green, and sustainable.
LIPID NANOPARTICLE COMPOSITION
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Paragraph 00393, (2021/10/15)
Provided herein are lipids that can be used in combination with other lipid components, such as neutral lipids, cholesterol and polymer conjugated lipids, to form lipid nanoparticles for delivery of therapeutic agents (e.g., nucleic acid molecules) for therapeutic or prophylactic purposes, including vaccination.
Visible-Light-Mediated Aerobic Oxidative C(sp3)?C(sp3) Bond Cleavage of Morpholine Derivatives Using 4CzIPN as a Photocatalyst
Dong, Chun-Lin,Huang, Lan-Qian,Guan, Zhi,Huang, Chu-Sheng,He, Yan-Hong
, p. 3803 - 3811 (2021/06/28)
Herein, a metal-free strategy for the aerobic oxidative cleavage of the inert C(sp3)?C(sp3) bond was developed. Deconstruction of morpholine derivatives was conducted using visible light as an energy source and O2 as an oxidant under mild conditions. This procedure demonstrated suitable selectivity and functional group tolerance. Moreover, a possible mechanism involving a radical process was proposed based on a series of mechanism exploration and control experiments. (Figure presented.).
Scalable preparation of stable and reusable silica supported palladium nanoparticles as catalysts for N-alkylation of amines with alcohols
Alshammari, Ahmad S.,Natte, Kishore,Kalevaru, Narayana V.,Bagabas, Abdulaziz,Jagadeesh, Rajenahally V.
, p. 141 - 149 (2020/01/06)
The development of nanoparticles-based heterogeneous catalysts continues to be of scientific and industrial interest for the advancement of sustainable chemical processes. Notably, up-scaling the production of catalysts to sustain unique structural features, activities and selectivities is highly important and remains challenging. Herein, we report the expedient synthesis of Pd-nanoparticles as amination catalysts by the reduction of simple palladium salt on commercial silica using molecular hydrogen. The resulting Pd-nanoparticles constitute stable and reusable catalysts for the synthesis of various N-alkyl amines using borrowing hydrogen technology without the use of any base or additive. By applying this Pd-based catalyst, functionalized and structurally diverse N-alkylated amines as well as some selected drug molecules were synthesized in good to excellent yields. Practical and synthetic utility of this Pd-based amination protocol has been demonstrated by upscaling catalyst preparation and amination reactions to several grams-scales as well as recycling of catalyst. Noteworthy, this Pd-catalyst preparation has been up-scaled to kilogram scale and catalysts prepared in both small (1 g) and large-scale (kg) exhibited similar structural features and activity.
Green synthesis of N-(2-hydroxyethyl)anilines by the selective alkylation reaction in H2O
Guo, Hui,Hao, Jia,Sun, Tingting,Wang, Zuoyao,Cao, Jian,Zhang, Guobao
, p. 1 - 6 (2020/07/21)
Based on our previous work, a safer and more sustainable protocol for the synthesis of N-(2-Hydroxyethyl)anilines has been developed. The synthesis included the selective alkylation reaction of aniline with 2-chloroethanol in H2O, eliminating the need for any catalysts and solvents during synthesis. Comparing with our previous work, the salient features of this methodology are eco-friendliness, economic benefit, and the ease of obtaining target compounds. The selective alkylation reaction in H2O is amenable to scale-up for the synthesis of N-(2-Hydroxyethyl)anilines.
Visible light-mediated Smiles rearrangements and annulations of non-activated aromatics
Lawson, Connor A.,Dominey, Andrew P.,Williams, Glynn D.,Murphy, John A.
supporting information, p. 11445 - 11448 (2020/10/12)
We report the first examples of radical cation Smiles rearrangements. A series of aryloxy alkylamines underwent spontaneous reaction, with the amino group displacing theipso-alkoxy group through substitution, at ambient temperature and under photoactivation by visible light in the presence of an acridinium catalyst (5 mol%). The study was extended to 3-(2-methoxyphenyl)propan-1-amine derivatives, which lack an appropriateipsoleaving group. Here, efficient cyclisations resulted in displacement of the methoxy group and formation of tetrahydroquinolines.
Ir(bis-NHC)-Catalyzed Direct Conversion of Amines to Alcohols in Aqueous Glycerol
Cheong, Yeon-Joo,Lee, Seunghyeon,Hwang, Sang Joon,Yoon, Woojin,Yun, Hoseop,Jang, Hye-Young
supporting information, p. 1940 - 1943 (2019/02/25)
Sustainable catalytic conversion of amines to alcohols was realized in the presence of iridium catalysts and aqueous glycerol. Iridium catalysts involving bis-N-heterocyclic carbene (bis-NHC) show good reactivity and stability in the conversion of amines into alcohols in aqueous glycerol. The reaction was initiated with the dehydrogenation of amines and followed by hydrolysis and reduction. Iridium catalysts play dual roles in both the dehydrogenation and reduction steps. By employing glycerol as a solvent and hydrogen source, the final reduction was facilitated. The synthesis and characterization of various Ir(bis-NHC) complexes are described along with the catalytic reaction results of the amine into alcohol conversion.
