Cabello-Sanchez, Noemi; Jean, Ludovic; Maddaluno, Jacques; Lasne, Marie-Claire; Rouden, Jacques published the article 《Palladium-mediated N-arylation of heterocyclic diamines: insights into the origin of an unusual chemoselectivity》. Keywords: palladium arylation heterocyclic diamine chemoselectivity.They researched the compound: Piperidin-4-amine dihydrochloride( cas:35621-01-3 ).Recommanded Product: 35621-01-3. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:35621-01-3) here.
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.
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Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia