Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: Piperidin-4-amine dihydrochloride, is researched, Molecular C5H14Cl2N2, CAS is 35621-01-3, about Palladium-mediated N-arylation of heterocyclic diamines: insights into the origin of an unusual chemoselectivity.Recommanded Product: 35621-01-3.
The chemoselectivity of the palladium-mediated reaction of bromobenzene with various heterocyclic diamines was studied. Whatever the ligand used, 3-aminopyrrolidine underwent arylation of the secondary amine function (>82%), whereas the more flexible 3-aminoazepine was arylated on its primary function (>70%). The ratio “”arylation of primary amine vs. arylation of secondary amine”” of 3-aminopiperidine with bromobenzene varied from 90:10 (BINAP, electron-enriched and hindered biphenyls L2 or L3) to 32:68 with the Josiphos-type ligand L10. The same trend was observed when 4-aminopiperidine was used (82:18 with L2 and 17:83 with L10). This selectivity can be tuned by the choice of aryl halide partners having different steric and electronic properties. A cooperative effect of both nitrogens of diamines during the reaction was deduced from competitive experiments Finally, 13C and 31P NMR experiments, carried out with 3-aminopyrrolidine at room temperature, support a fast coordination of the primary amine to the metal. Indeed, a palladium complex resulting from the unusual displacement of one phosphine group of the intermediate ArPdX(BINAP) by the primary amino group was characterized.
There is still a lot of research devoted to this compound(SMILES：NC1CCNCC1.[H]Cl.[H]Cl)Recommanded Product: 35621-01-3, and with the development of science, more effects of this compound(35621-01-3) can be discovered.
Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia