908600-05-5Relevant academic research and scientific papers
A silica-supported titanium catalyst for heterogeneous hydroamination and multicomponent coupling reactions
Aldrich, Kelly E.,Odom, Aaron L.
, p. 11352 - 11360 (2019/08/07)
Highly dehydrated silica gel, SiO2700, gave a material with a total surface hydroxyl density of 0.31 ± 0.05 mmol g-1, 0.9 ± 0.1 Si-OH sites per nm2. Treatment of this material with Ti(NMe2)4/sub
Titanium-Catalyzed Hydroamination and Multicomponent Coupling with a Simple Silica-Supported Catalyst
Aldrich, Kelly E.,Odom, Aaron L.
, p. 4341 - 4349 (2019/01/03)
Hydroamination and multicomponent coupling reactions catalyzed by homogeneous Ti(IV) complexes can produce valuable imines, amines, and other nitrogen-containing organic building blocks. Typically catalysts for this transformation are very sensitive to an
A general study of [(η5-Cp′)2Ti(η 2-Me3SiC2SiMe3)]-catalyzed hydroamination of terminal alkynes: Regioselective formation of Markovnikov and anti-Markovnikov products and mechanistic explanation (Cp′=C (5)H(5), C(5)H(4)Et, C(5)Me(5))
Tillack, Annegret,Jiao, Haijun,Castro, Ivette Garcia,Hartung, Christian G.,Beller, Matthias
, p. 2409 - 2420 (2007/10/03)
A general study of the regioselective hydroamination of terminal alkynes in the presence of [(η5-Cp)2Ti(η2-Me 3SiC2SiMe3)] (1), [(η5-CpEt) 2Ti(η2-Me3SiC2SiMe3)] (CpEt= ethylcyclopentadienyl) (2), and [(η5-Cp*) 2Ti(η2-Me3SiC2SiMe3)] (Cp=pentamethylcyclopentadienyl) (3) is presented. While aliphatic amines give mainly the anti-Markovnikov products, anilines and aryl hydrazines yield the Markovnikov isomer as main products. Interestingly, using aliphatic amines such as n-butylamine and benzylamine the different catalysts lead to a significant change in the observed regioselectivity. Here, for the first time a highly selective switch from the Markovnikov to the anti-Markovnikov product is observed simply by changing the catalyst. Detailed theoretical calculations for the reaction of propyne with different substituted anilines and tert-butylamine in the presence of [(η5-C5H5)Ti(= NR)(NHR)] (R=4-C6H4X; X=H, F, Cl, CH3, 2,6-dimethylphenyl) reveal that the experimentally observed regioselectivity is determined by the relative stability of the corresponding π-complexes 10. While electrostatic stabilization favors the Markovnikov performance for aniline, the steric repulsive destabilization disfavors the Markovnikov performance for tert-butylamine.
Ketoform reaction. Synthesis of hindered imines from 2,6-dialkylanilines and ketones
Lai, John T
, p. 1965 - 1967 (2007/10/03)
Hindered imines are synthesized from 2,6-dialkylanilines, ketones, chloroform and sodium hydroxide in a phase-transfer catalyzed reaction.
