13541-00-9Relevant articles and documents
Switching Selectivity in Copper-Catalyzed Transfer Hydrogenation of Nitriles to Primary Amine-Boranes and Secondary Amines under Mild Conditions
Song, Hao,Xiao, Yao,Zhang, Zhuohua,Xiong, Wanjin,Wang, Ren,Guo, Liangcheng,Zhou, Taigang
, p. 790 - 800 (2022/01/11)
A simple and efficient copper-catalyzed selective transfer hydrogenation of nitriles to primary amine-boranes and secondary amines with an oxazaborolidine-BH3 complex is reported. The selectivity control was achieved under mild conditions by switching the solvent and the copper catalysts. More than 30 primary amine-boranes and 40 secondary amines were synthesized via this strategy in high selectivity and yields of up to 95%. The strategy was applied to the synthesis of 15N labeled in 89% yield.
Synthesis, characterization, and antibacterial activity of dibenzildithiocarbamate derivates and Ni(II)–Cu(II) coordination compounds
Amaya-Flórez, Andres,Aranaga, Carlos,D'Vries, Richard F.,Ellena, Javier,Flórez-López, Edwin,Macías, Mario,Pastrana-Dávila, Andrea
, (2021/07/28)
In this work, the study of the synthesis methodology to obtain dibenzylamine derivates as intermediates for the formation of dithicarbamate ligands (DTC) and its coordination compounds was conducted. Four molecules derived from dibenzylamine were synthesized by two methodologies: classical (reflux) and microwave. From these amines, Four dithiocarbamate ligands (DTC): dibenzyldithiocarbamate, N-benzyl-1-(4-methoxyphenyl)dithiocarbamate, N-benzyl-1-(4-chlorophenyl)dithiocarbamate, and N-benzyl-1-(3-nitrophenyl)dithiocarbamate, and eight coordination complexes with general formula [M(DTC)2]nH2O (M= Cu(II) and Ni(II)) were obtained. All the compounds were characterized using different spectroscopic and thermal techniques such as Fourier-transform infrared spectroscopy (FT-IR), ultraviolet–visible spectroscopy (UV–VIS), proton and carbon-13 nuclear magnetic resonance (1H and 13C NMR), thermogravimetric analysis–differential scanning calorimetry (TGA-DSC). Additionally, it was possible to characterize two new crystalline phases of salts through single-crystal X-ray diffraction: dibenzyl ammonium nitrate and N-benzyl-1-(3-nitrophenyl)ammonium chloride. Additionally, microbial inhibition tests were conducted using the dibenzildithiocarbamate derivates. All DTC compounds showed important activity against Pseudomonas aeruginosa and Staphylococcus aureus but less sensitivity against Escherichia coli and Mycobacterium smegmatis. Among the coordination compounds, only [Cu(N-benzyl-1-(3-nitrophenyl)dithiocarbamate)2] presented a moderate activity against M. smegmatis mc2 155.
Phosphine-Free Manganese Catalyst Enables Selective Transfer Hydrogenation of Nitriles to Primary and Secondary Amines Using Ammonia-Borane
Sarkar, Koushik,Das, Kuhali,Kundu, Abhishek,Adhikari, Debashis,Maji, Biplab
, p. 2786 - 2794 (2021/03/03)
Herein we report the synthesis of primary and secondary amines by nitrile hydrogenation, employing a borrowing hydrogenation strategy. A class of phosphine-free manganese(I) complexes bearing sulfur side arms catalyzed the reaction under mild reaction conditions, where ammonia-borane is used as the source of hydrogen. The synthetic protocol is chemodivergent, as the final product is either primary or secondary amine, which can be controlled by changing the catalyst structure and the polarity of the reaction medium. The significant advantage of this method is that the protocol operates without externally added base or other additives as well as obviates the use of high-pressure dihydrogen gas required for other nitrile hydrogenation reactions. Utilizing this method, a wide variety of primary and symmetric and asymmetric secondary amines were synthesized in high yields. A mechanistic study involving kinetic experiments and high-level DFT computations revealed that both outer-sphere dehydrogenation and inner-sphere hydrogenation were predominantly operative in the catalytic cycle.
