16183-21-4Relevant academic research and scientific papers
Polyoxometalate-Driven Ease Conversion of Valuable Furfural to trans- N, N-4,5-Diaminocyclopenten-2-ones
Fountoulaki, Stella,Lykakis, Ioannis N.,Tzani, Marina A.
, (2022/02/10)
We investigated the catalytic efficacy of silicotungstic acid (H4SiW12O40) polyoxometalate (POM) toward the reaction between furfural and amines that selectively yields trans-N,N-4,5-substituted-diaminocyclopenten-2-ones (trans-DACPs). H4SiW12O40 facilita
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.
Generation of Aminyl Radicals using Sulfenamides as Synthetic Precursors
Bowman, W. Russell,Clark, David N.,Marmon, Robert J.
, p. 1275 - 1294 (2007/10/02)
Sulfenamides are synthesised from reaction between amines and N-(benzenesulfenil)-phthalimide or benzenesulfenyl chloride.The sulfenamides undergo reaction with tributyltin hydride to yield aminyl radicals which can be cyclised onto suitable alkenes. Key Words: sulfenamides; aminyl radicals; tributyltin hydride; radical-cyclisation; N-(benzenesulfenyl)phthalimide
Sulphenamides as synthetic precursors of aminyl radicals
Bowman, W.Russell,Clark, David N.,Marmon, Robert J.
, p. 6441 - 6444 (2007/10/02)
Sulphenamides, readily synthesised from reaction between benzenesulphenyl derivatives and amines, undergo facile reaction with radical generating reagents such as tributyltin hydride to yield aminyl radicals.
EFFECTS OF SUBSTITUENTS IN THE BENZYL BROMIDE ON THE KINETICS OF THE BENZYLATION OF AMINES
Shpan'ko, I. V.,Korostylev, A. P.,Rusu, L. N.
, p. 1715 - 1723 (2007/10/02)
The kinetics of the reactions of 3- and 4-substituted benzyl bromides with amines having various structures in nitrobenzene at 40 deg C were investigated.The 4-substituted benzyl bromides have higher reactivity compared with that calculated on the basis of the linear correlations according to the Hammett-Taft equation for unsubstituted and 3-substituted benzyl bromides containing electron-withdrawning substituents.The reactivity of benzyl bromides containing electron-donating substituents obeys a linear correlation with the ?+ constants.The effects of structural changes in the substrate and the nucleophile on the character of the transition states of the investigated reactions is discussed.
