Chemistry is an experimental science, Application In Synthesis of 3-Aminohomopiperidine, and the best way to enjoy it and learn about it is performing experiments.Introducing a new discovery about 69154-03-6, Name is 3-Aminohomopiperidine
Palladium-mediated N-arylation of heterocyclic diamines: Insights into the origin of an unusual chemoselectivity
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-aminoazepinine was arylated on its primary function (>70%). The ratio “arylation of primary amine versus 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 phosphane group of the intermediate ArPdX(BINAP) by the primary amino group was characterized.
Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. Application In Synthesis of 3-Aminohomopiperidine, If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 69154-03-6, in my other articles.
Reference£º
Piperidine – Wikipedia,
Piperidine | C5H2228N – PubChem