1203602-87-2Relevant academic research and scientific papers
Ligand acceleration in ZnI2-catalyzed intramolecular hydroamination of unfunctionalized olefins
Liu, Gong-Qing,Li, Wei,Wang, Yu-Mei,Ding, Zhen-Ying,Li, Yue-Ming
, p. 4393 - 4396 (2012/09/22)
Zinc halide-promoted hydroamination of 4-penten-1-amine compounds was studied. Preliminary results indicated that both steric and electronic factors are crucial for this Lewis acid-promoted reaction. ZnI2 gave the most promising results and the reactivity could be further increased upon addition of a suitable ligand. Up to 95% isolated yields were obtained when the reactions were carried out in 1,4-dioxane in the presence of 10 mol % of ZnI2 and 8-hydroxyquinoline.
Broadening the scope of group 4 hydroamination catalysis using a tethered ureate ligand
Leitch, David C.,Payne, Philippa R.,Dunbar, Christine R.,Schafer, Laurel L.
supporting information; experimental part, p. 18246 - 18247 (2010/04/25)
(Chemical Equation Presented) A broadly applicable group-4-based precatalyst for the hydroamination of primary and secondary amines was developed. Screening experiments involving a series of amide and urea proligands led to the discovery of a tethered bis(ureate) zirconium complex with unprecedented reactivity in the intermolecular hydroamination of alkynes and the intramolecular hydroamination of alkenes. This catalyst system is effective with primary and secondary amines, 1,2-disubstituted alkenes, and heteroatom-containing functional groups, including ethers, silanes, amines, and heteroaromatics. The gem-disubstituent effect is not required for cyclization. The catalyst is generally regioselective for the anti-Markovnikov product of intermolecular alkyne hydroamination, and chemoselective for hydroamination over C-alkylation when forming 6- and 7-membered rings from aminoalkenes.
