The selective N-monomethylation of primary anilines was realized by the use of the Me3N-BH3/N,N-dimethylformamide (DMF) system as the methyl source. This method also allows for the controllable introduction of N-CH2D, N-CHD2, and N-CD3 units with high levels of deuterium incorporation using Me3N-BH3/d7-DMF, Me3N-BD3/DMF and Me3N-BD3/d7-DMF systems, respectively.
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http://dx.doi.org/10.1039/d0ob01054e | DOI Listing |
Chemistry
November 2024
Amity Institute of Applied Sciences, Amity University, Uttar Pradesh, Noida, 201313, India.
N-monomethyl amines are useful intermediates in drugs, natural products, paints. Yet their synthesis is a tremendous challenge due to their high reactivity, typically leading to overmethylation. In this contribution, a highly selective catalytic N-methylation methodology is reported, converting urea derivatives to monomethylated amines, using a commercially available heterogeneous Pd/C catalyst and methanol as unique reagent.
View Article and Find Full Text PDFMolecules
April 2024
Dipartimento di Chimica, Università Degli Studi di Milano, Via Golgi 19, 20133 Milan, Italy.
Borane-trimethylamine complex (MeN·BH; BTM) is the most stable of the amine-borane complexes that are commercially available, and it is cost-effective. It is a valuable reagent in organic chemistry with applications in the reduction of carbonyl groups and carbon-nitrogen double bond reduction, with considerable examples in the reduction of oximes, hydrazones and azines. The transfer hydrogenation of aromatic -heterocycles and the selective -monomethylation of primary anilines are further examples of recent applications, whereas the reduction of nitrobenzenes to anilines and the reductive deprotection of -tritylamines are useful tools in the organic synthesis.
View Article and Find Full Text PDFBiomacromolecules
May 2023
Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland.
Cationic polymers have been extensively investigated as a potential replacement for traditional antibiotics. Here, we examined the effect of molecular weight (MW) on the antimicrobial, cytotoxic, and hemolytic activity of linear polytrimethylenimine (L-PTMI). The results indicate that the biological activity of the polymer sharply increases as MW increases.
View Article and Find Full Text PDFOrg Biomol Chem
July 2020
Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.
The selective N-monomethylation of primary anilines was realized by the use of the Me3N-BH3/N,N-dimethylformamide (DMF) system as the methyl source. This method also allows for the controllable introduction of N-CH2D, N-CHD2, and N-CD3 units with high levels of deuterium incorporation using Me3N-BH3/d7-DMF, Me3N-BD3/DMF and Me3N-BD3/d7-DMF systems, respectively.
View Article and Find Full Text PDFOrg Lett
July 2018
Department of Chemical Science and Engineering, School of Materials and Chemical Technology , Tokyo Institute of Technology, 2-12-1-E4-1 O-okayama , Meguro-ku , Tokyo 152-8552 , Japan.
The use of methanol for the selective methylation of aromatic amines with RuHCl(CO)(PNP) (PNP = bis(2-diphenylphosphinoethyl)amine) is reported. Various aromatic amines were transformed into their corresponding monomethylated secondary amines in high yields at 150 °C with a very low catalyst loading (0.02-0.
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