17279-31-1Relevant articles and documents
Monson,Priest
, p. 3826 (1971)
Vitt,Khristova
, (1971)
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Bach,R.D.
, p. 1647 - 1649 (1968)
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N-Methylation of Amines with Methanol at Room Temperature
Tsarev, Vasily N.,Morioka, Yuna,Caner, Joaquim,Wang, Qing,Ushimaru, Richiro,Kudo, Akihiko,Naka, Hiroshi,Saito, Susumu
, p. 2530 - 2533 (2015)
N-Methylation of amines with methanol proceeds at room temperature in the presence of a silver-loaded titanium dioxide (Ag/TiO2) photocatalyst under UV-vis light irradiation. This method allows facile synthesis/isolation of N-methylamines bearing various functional groups including N-benzyl, N-allyl, N-Boc, hydroxyl, ether, acetal, carboxamide, formamide, and olefin groups. (Chemical Presented)
Studies on the configuration of nitrogenous stereogenic centres in adducts of rhodium(II) tetraacylates with chiral amines: the application of 1H and 13C NMR spectroscopy
Jazwinski, Jaroslaw,Sadlej, Agnieszka
, p. 2331 - 2343 (2009)
The 1H and 13C NMR spectra of enantiomerically pure amines (S)-N,N-dimethyl-1-phenylethylamine, (S)-N-methyl-1-phenylethylamine, (S)-N-ethyl-1-phenylethylamine and (S)-N-ethyl-N-methyl-1-phenylethylamine in the presence of a twofold molar excess of dirhodium(II) tetratrifluoroacetate and dirhodium(II) Mosher's acid derivatives [(4S) and (4R)] were measured in CDCl3 as a solvent. The amines having various substituents at the nitrogen atom (H, CH3 and CH2CH3) formed in such conditions as an equilibrium mixture of CSNR and CSNS 1:1 adducts. The signals of both diastereoisomers were observed in NMR spectra at either room temperature (303 K) or moderately decreased temperatures (263-273 K). The rates of mutual diastereoisomer conversion were estimated by selective inversion recovery experiments and varied from less than 0.1 to ca. 10 s-1, depending on the ligand and temperature. Analysis of 13C NMR data and NOE experimental data resulted in the unambiguous determination of the configuration at the nitrogen atom with respect to the carbon stereogenic centre. Modelling of adduct structures and calculations of molecular energy and NMR parameters (GIAO) using Density Functional Theory (DFT) were performed in order to support the experimental findings. The calculations were carried out using 3-21G//B3LYP (structure optimizing) and 311G(2d,p)/LanL2DZ//B3LYP theory levels (molecular energy and NMR shielding).
Preparation method of N-alkylated derivative of primary amine compound
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Paragraph 0021; 0053, (2021/07/09)
The invention relates to a preparation method of an N-alkylated derivative of a primary amine compound. The method comprises the following steps: uniformly mixing a primary amine compound, an alcohol compound and a catalyst in a reactor, and heating to react for a period of time to generate an N-alkylated substituted tertiary amine compound; wherein the catalyst is a copper-cobalt bimetallic catalyst, and the carrier of the catalyst is Al2O3. According to the method, alcohol is adopted as an alkylating reagent and is low in price and easy to obtain, a byproduct is water, no pollution is caused to the environment, and the overall reaction atom economy is high; the catalyst is simple in preparation method, low in cost, high in reaction activity and good in structural stability; meanwhile, by using the copper-cobalt bimetallic catalyst, the use of strong base additives can be avoided, and the requirement on reaction equipment is low; and the reaction post-treatment is convenient, and the catalyst can be recycled and is environment-friendly.
Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates
Chattopadhyay, Buddhadeb,Hassan, Mirja Md Mahamudul,Hoque, Md Emdadul
supporting information, p. 5022 - 5037 (2021/05/04)
Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.