103391-83-9Relevant academic research and scientific papers
Two-Step Procedure for the Synthesis of 1,2,3,4-Tetrahydro-quinolines
Doye, Sven,Warsitz, Michael
, p. 6997 - 7014 (2020/12/01)
A new two-step procedure that includes an initial regioselective intermolecular hydroaminoalkylation of ortho-chlorostyrenes with N-methylanilines and a subsequent intramolecular Buchwald–Hartwig amination gives direct access to 1,2,3,4-tetrahydroquinolines. The hydroaminoalkylation reaction of the ortho-chlorostyrenes is catalyzed by a 2,6-bis(phenylamino)pyridinato titanium complex which delivers the linear regioisomers with high selectivities. In addition, the formation of unexpected dihydroaminoalkylation products from styrenes and N-methylanilines is reported.
Regioselective hydroaminomethylation of vinylarenes by a sol-gel immobilized rhodium catalyst
Nairoukh, Zackaria,Blum, Jochanan
, p. 2397 - 2403 (2014/04/17)
In the course of our studies toward the development of new heterogeneous conditions for better controlling regioselectivity in organic reactions, we investigated the application of sol-gel immobilized organometallic catalyst for regioselective hydroaminomethylation of vinylarenes with aniline or nitroarene derivatives in an aqueous microemulsion. By immobilization of 6 mol % [Rh(cod)Cl]2 within a hydrophobic silica sol-gel matrix we were able to perform efficient hydroaminomethylation under mild conditions and isolate 2-arylpropylamines with high regioselectivity. The regioselectivity of the reaction was found to be mainly dependent on the hydrophobicity of the catalyst support. It is also significantly affected by the electronic nature of the substrates, by the reaction temperature, and by syngas pressure. The heterogenized catalyst can be reused for several times.
