41215-40-1Relevant articles and documents
Multicomponent Ugi Reaction of Indole- N-carboxylic Acids: Expeditious Access to Indole Carboxamide Amino Amides
Zeng, Linwei,Sajiki, Hironao,Cui, Sunliang
supporting information, p. 5269 - 5272 (2019/07/03)
A novel multicomponent Ugi-type reaction for the synthesis of indole carboxamide amino amides from aldehydes, amines, isocyanides, and indole-N-carboxylic acids, which were simply prepared from indoles and CO2, is described. This method provides an expeditious and practical access to indole tethered peptide units, along with the achievement of remarkable structural diversity and brevity. Gram-scale reaction was conducted to demonstrate the scalability, and the products could be transformed to new indole derivatives.
Amine formylation with CO2 and H2 catalyzed by heterogeneous Pd/PAL catalyst
Dai, Xingchao,Wang, Bin,Wang,Shi, Feng
, p. 1141 - 1146 (2019/07/09)
For the first time, Pd supported on natural palygorskite was developed for amine formylation with CO2 and H2. Both secondary and primary amines with diverse structures could be converted into the desired formamides at 100 °C, and good to excellent yields were obtained.
Rapid synthesis method of biomass-based amide
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Paragraph 0064-0066; 0069, (2019/01/15)
The invention discloses a rapid synthesis method of biomass-based amide, which comprises the steps: formamide is used as an amine source, formic acid is used as a hydrogen source, biomass aldehyde andketone is used as a raw material, the direct addition of formamide and aldehyde and ketone components and the reduction of formic acid is promoted to prepare the corresponding formamide derivative byrapidly heating under microwave-assisted heating and in the absence of a solvent and a catalyst; the formamide derivative is selectively converted to the corresponding primary amide by alcoholysis under the action of a base. The microwave assisted heating reaction system of the invention has higher catalytic efficiency than the corresponding oil bath system, greatly shortens the reaction time, remarkably improves the selectivity. The conversion rate of the biomass aldehyde or ketone compound is at least 99%, and the yield of the formamide derivative can reach 85 to 99%; the formamide can be synthesized by alcoholysis to obtain a primary amide with a yield of 92 to 99%.
N-doped carbon supported Pd catalysts for N-formylation of amines with CO2/H2
Luo, Xiaoying,Zhang, Hongye,Ke, Zhengang,Wu, Cailing,Guo, Shien,Wu, Yunyan,Yu, Bo,Liu, Zhimin
, p. 725 - 731 (2018/04/02)
Using mesoporous N-doped carbons (NCs) derived from glucose and melamine as the supports, a series of Pd/NC catalysts were prepared, in which Pd nanoparticles with average size2 and H2 in ethanol without any additives. Especially, the catalyst Pd/NC-800-6.9% containing quaternary N showed the best performance, affording a series of formylamides in good or even excellent yields. Further investigation reveals that the interaction between the Pd nanoparticles and quaternary nitrogen in the NC support was responsible for the good performance of the catalyst.
Ethanol-mediated N-formylation of amines with CO2/H2 over cobalt catalysts
Liu, Zhenghui,Yang, Zhenzhen,Ke, Zhengang,Yu, Xiaoxiao,Zhang, Hongye,Yu, Bo,Zhao, Yanfei,Liu, Zhimin
, p. 13933 - 13937 (2018/08/21)
The CO2-involved synthesis of chemicals is of great significance from a green and sustainable point of view. Herein, we present an efficient Co-based catalytic system composed of a commercially available Co salt, the tetradentate phosphine ligand P-(CH2CH2PPh2)3, and a base, denoted as [Co]/PP3/base, for the synthesis of formamides via the formylation of amines with CO2/H2. It was indicated that the selectivity of products (i.e., formamide or methylamine) could be tuned to some extent via changing the solvent and the base. Using ethanol as the solvent, the Co(ClO4)2·6H2O/PP3/K2CO3 system showed high activity for the production of formamides, affording product yields of 82-95%, together with its broad substrate scope. Exploration of the reaction mechanism indicated that formamide was formed with HCOOH as the intermediate, while the methylamine byproduct was produced with HCHO as the intermediate via the hydrogenolysis of dialkylaminomethane.
Production of Formamides from CO and Amines Induced by Porphyrin Rhodium(II) Metalloradical
Zhang, Jiajing,Zhang, Wentao,Xu, Minghui,Zhang, Yang,Fu, Xuefeng,Fang, Huayi
supporting information, p. 6656 - 6660 (2018/05/24)
It is of fundamental importance to transform carbon monoxide (CO) to petrochemical feedstocks and fine chemicals. Many strategies built on the activation of C≡O bond by π-back bonding from the transition metal center were developed during the past decades. Herein, a new CO activation method, in which the CO was converted to the active acyl-like metalloradical, [(por)Rh(CO)]? (por = porphyrin), was reported. The reactivity of [(por)Rh(CO)]? and other rhodium porphyrin compounds, such as (por)RhCHO and (por)RhC(O)NHnPr, and corresponding mechanism studies were conducted experimentally and computationally and inspired the design of a new conversion system featuring 100% atom economy that promotes carbonylation of amines to formamides using porphyrin rhodium(II) metalloradical. Following this radical based pathway, the carbonylations of a series of primary and secondary aliphatic amines were examined, and turnover numbers up to 224 were obtained.
Ru/ceria-catalyzed direct formylation of amines and CO to produce formamides
Wang, Yehong,Zhang, Jian,Chen, Haijun,Zhang, Zhixin,Zhang, Chaofeng,Li, Mingrun,Wang, Feng
, p. 88 - 92 (2017/01/24)
We herein report a new strategy of directly converting amines and CO to formamides with 100% atom utilization efficiency. It is suitable for up to 25 amine substrates with no additives. Ru/ceria is found to be an excellent catalyst for this reaction due the efficient co-activation of CO and amine on Ru species.
Preparation method for methanamide
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Paragraph 0043; 0044, (2017/05/26)
The invention relates to a method for preparing methanamide compounds through carbonylation of amine. The method employs primary amine or secondary amine and carbon monoxide (CO) as reactants and prepares the methanamide compounds through a CO-inserted carbonylation reaction under the catalysis of ruthenium-loaded hydroxyapatite (Ru/HAP). Reaction conditions are that the reaction is carried out in a tank reactor under stirring; CO pouring pressure is 0.5 to 5.0 MPa; and reaction temperature is 100 to 200 DEG C. The method has the characteristics that (1) the reaction has 100% atom economy and is free of generation of any by-product; (2) the ruthenium-loaded hydroxyapatite is used as a catalyst, the catalyst is simple to prepare and efficiently catalyzes the reaction, and the yield of the methanamide compounds can reach 80% or above; and (3) the catalyst has good stability and can be cyclically used four times or more.
Supported nano-gold-catalyzed N-formylation of amines with paraformaldehyde in water under ambient conditions
Ke, Zhengang,Zhang, Yan,Cui, Xinjiang,Shi, Feng
, p. 808 - 816 (2016/02/12)
A simple and efficient Au/Al2O3 catalyst was prepared by the co-precipitation method for the oxidative N-formylation of amines with paraformaldehyde. Under the optimized reaction conditions, excellent amine conversion and N-formamide selectivity can be obtained with up to 97% yield with water as the solvent under ambient conditions. This catalyst tolerated a wide range of primary amines and second amines, and it can be reused for at least five runs without obvious deactivation.
C-N and N-H Bond Metathesis Reactions Mediated by Carbon Dioxide
Wang, Yehong,Zhang, Jian,Liu, Jing,Zhang, Chaofeng,Zhang, Zhixin,Xu, Jie,Xu, Shutao,Wang, Fangjun,Wang, Feng
, p. 2066 - 2072 (2015/06/30)
Herein, we report CO2-mediated metathesis reactions between amines and DMF to synthesize formamides. More than 20 amines, including primary, secondary, aromatic, and heterocyclic amines, diamines, and amino acids, are converted to the corresponding formamides with good-to-excellent conversions and selectivities under mild conditions. This strategy employs CO2 as a mediator to activate the amine under metal-free conditions. The experimental data and in situ NMR and attenuated total reflectance IR spectroscopy measurements support the formation of the N-carbamic acid as an intermediate through the weak acid-base interaction between CO2 and the amine. The metathesis reaction is driven by the formation of a stable carbamate, and a reaction mechanism is proposed.
