606-99-5Relevant academic research and scientific papers
N -Arylation of (hetero)arylamines using aryl sulfamates and carbamates via C-O bond activation enabled by a reusable and durable nickel(0) catalyst
Dindarloo Inaloo, Iman,Majnooni, Sahar,Eslahi, Hassan,Esmaeilpour, Mohsen
, p. 13266 - 13278 (2020/10/07)
An effective and general aryl amination protocol has been developed using a magnetically recoverable Ni(0) based nanocatalyst. This new stable catalyst was prepared on Fe3O4@SiO2 modified by EDTA and investigated by FT-IR, EDX, TEM, XRD, DLS, FE-SEM, XPS, NMR, TGA, VSM, ICP and elemental analysis techniques. The reaction proceeded via carbon-oxygen bond cleavage of (hetero)aryl carbamates and sulfamates under simple and mild conditions without the use of any external ligands. This method demonstrated functional group tolerance in the N-arylation of various nitrogen-containing compounds as well as aliphatic amines, anilines, pyrroles, pyrazoles, imidazoles, indoles, and indazoles with good to excellent yields. Furthermore, the catalyst could be easily recovered by using an external magnetic field and directly reused at least six times without notable reduction in its activity. This journal is
A simple method for the synthesis of sulfonic esters
Bhatthula, Bharath Kumar Goud,Kanchani, Janardhan Reddy,Arava, Veera Reddy,Marata Chenna Subbarao, Subha
supporting information, p. 1 - 16 (2020/07/27)
An efficient and simple approach for the direct synthesis of aryl and heteroaryl sulfonic esters was developed using DMS and DES as alkoxysulfonylation reagents. The reaction is operationally simple and scalable. This protocol does not require solvent, expensive catalysts, base, ligand additives or other reagents. A wide range of sulfonic esters were synthesized in moderate to good chemical yields. This method has the advantage of low cost, facile and tolerated a wide range of substrates.
Transition-Metal-Free Three-Component Synthesis of Tertiary Aryl Amines from Nitro Compounds, Boronic Acids, and Trialkyl Phosphites
Roscales, Silvia,Csáky, Aurelio G.
supporting information, p. 111 - 117 (2019/11/16)
The synthesis of aromatic amines is of continuous interest in chemistry. An exceptionally versatile three-component reaction that directly transforms inexpensive nitro compounds, boronic acids, and trialkyl phosphites into tertiary aromatic amines has been realized. The reaction tolerates alkyl and aryl substituents on the nitro and boronic acid moieties, as well as functionalized phosphites. No transition-metal catalysis is required. The method is orthogonal to other classical metal-catalyzed syntheses since it tolerates the presence of halogens, and also permits the synthesis of functionalized compounds such as α-amino ester derivatives. (Figure presented.).
Iron-Catalyzed Synthesis of 2-Aminofurans from 2-Haloketones and Tertiary Amines or Enamines
Wang, Le-Cheng,Geng, Hui-Qing,Peng, Jin-Bao,Wu, Xiao-Feng
supporting information, p. 2605 - 2616 (2020/04/24)
The selective synthesis of heterocycles from readily available substrates and catalyzed by an abundant and environmental benign catalyst continues to be an attractive topic. In this communication, we report an interesting protocol for the synthesis of 2-aminofurans. Starting from 2-haloketones and tertiary amines, with abundant iron salt as the catalyst, various 2-aminofurans were produced in good yields. Control experiments were performed to understand the reaction pathway. Based on the identified reaction pathway, the substrates for this transformation can be extended from tertiary amines to enamines and even with better final yields. Finally, a formal three-component reaction can also be realized by forming the enamines in-situ from aldehydes and amines.
Recyclable bimetallic CuMoO4 nanoparticles for C-N cross-coupling reaction under mild conditions
Panigrahi, Reba,Panda, Subhalaxmi,Behera, Pradyota Kumar,Sahu, Santosh Kumar,Rout, Laxmidhar
supporting information, p. 19274 - 19278 (2019/12/24)
Herein we disclosed inexpensive copper(ii) bimetallic CuMoO4 nanoparticles for the C-N cross-coupling reaction of alkyl and aryl amines with haloarenes. The reaction proceeds under mild and ligand free conditions. The catalyst is recyclable and effective for a wide range of amines and haloarenes. Here, the efficiency of the Cu(ii) catalyst is increased by doping molybdenum metal. The bimetallic nanoparticles are anticipated to proceed via normal oxidative addition and reductive eliminations.
Solvent-free mechanochemical Buchwald-Hartwig amination of aryl chlorides without inert gas protection
Shao, Qiao-Ling,Jiang, Zhi-Jiang,Su, Wei-Ke
supporting information, p. 2277 - 2280 (2018/05/16)
A solvent-free Buchwald-Hartwig amination had been developed under high-speed ball-milling conditions, which afforded the desired products with moderate to high yields. The addition of sodium sulfate was found to be crucial for improving both the performance and the reproducibility. Comparative solvent-free stirring experiments implicated the importance of mechanical interaction for the transformation, and the inert gas was proved to be unnecessary for this amination.
A mechanical to urge the enters the carbon - [...] forming method (by machine translation)
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Paragraph 0042; 0043; 0044; 0046; 0059, (2018/09/21)
The invention discloses a mechanical to urge the enters the carbon - [...] forming method, said method comprising: in order to type 2 shown in formulae of organic amine 3 shown the chlorinated aromatic hydrocarbon as the raw material, the catalyst, ligand, in the presence of alkali and additive, the reaction is carried out by the mechanical grinding method, after the reaction mixture after the separation and purification, obtains the type 1 compound shown; in the present invention relates to mechanical grinding promotion to the chlorinated aromatic hydrocarbon as the substrate of the Buchwald - Hartwig reaction mainly adopts the organic phosphonate ligands, in the palladium catalyst under the action of the organic amine compound with the chlorinated aromatic hydrocarbon of the between the coupling, so as to obtain high yield of the target product, the majority of the reaction can be 90% or more yield. The mild reaction conditions, can be in the 1 - 2 H to complete the reaction. (by machine translation)
Nano CoCuFe2O4-catalyzed coupling reaction of arylboronic acid with amines and thiols: An atom-economic and ligand-free route to access unsymmetrical amines and sulfides
Moghaddam, Firouz Matloubi,Pourkaveh, Raheleh,Gholamtajari, Milad
, (2018/10/20)
An efficient protocol was developed for the nano CoCuFe2O4-catalyzed C-N and C-S bond formation. By this catalytic system, both amine and sulfide-based structural motifs were formed efficiently in aryl halide-free route. The amination reaction of phenyl boronic acid with various types of amines was conducted under ligand-free conditions, in ethanol as a green solvent at 60°C. Unsymmetrical diaryl/aryl alkyl sulfide synthesis via the coupling reaction of arylboronic acids with thiols was also conducted. The nano cobalt-copper ferrite was used as a heterogenous efficient, inexpensive, magnetically separable and recyclable catalyst that can be used for several cycles.
Direct arylation of tertiary amines via aryne intermediates using diaryliodonium salts
Zhang, Zhiang,Wu, Xunshen,Han, Jianwei,Wu, Wenjun,Wang, Limin
supporting information, p. 1737 - 1741 (2018/04/02)
With a strategy by using diaryliodonium salts as the precursors of benzynes, direct N-arylation of tertiary amines with diaryliodonium salts was reported. Thus, the desired aromatic tertiary amines with a wide range of substituents were synthesized in moderate to excellent yields of 55–91%.
Deoxygenation of tertiary amine N-oxides under metal free condition using phenylboronic acid
Gupta, Surabhi,Sureshbabu, Popuri,Singh, Adesh Kumar,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
supporting information, p. 909 - 913 (2017/02/15)
A simple and efficient method for the deoxygenation of amine N-oxides to corresponding amines is reported using the green and economical reagent phenylboronic acid. Deoxygenation of N,N-dialkylaniline N-oxides, trialkylamine N-oxides and pyridine N-oxides were achieved in good to excellent yields. The reduction susceptible functional groups such as ketone, amide, ester and nitro groups are well tolerated with phenylboronic acid during the deoxygenation process even at high temperature. In addition, an indirect method for identification and quantification of tert-amine N-oxide is demonstrated using UV–Vis spectrometry which may be useful for drug metabolism studies.
