940366-05-2Relevant academic research and scientific papers
A New N-Trityl-Substituted Aminopyridinato Titanium Catalyst for Hydroamination and Hydroaminoalkylation Reactions - Unexpected Intramolecular C-H Bond Activation
Lühning, Lars H.,Brahms, Christian,Nimoth, Jelte P.,Schmidtmann, Marc,Doye, Sven
, p. 2071 - 2082 (2015/10/19)
Sterically demanding 2,6-bis(tritylamino)pyridine is used for the synthesis of a mono(2,6-diaminopyridinato) titanium complex that undergoes unexpected intramolecular C-H bond activation to give access to an unusual 1-titanaisoindoline derivative. Both titanium complexes do not show high catalytic activity for hydroaminoalkylation reactions of alkenes but exceptional results are obtained in the field of alkene, alkyne, and allene hydroamination including room temperature activity for intramolecular alkene hydroamination, excellent regioselectivity of intermolecular alkyne and allene hydroamination as well as selectivity for hydroamination over hydroaminoalkylation during cyclization reactions of primary aminoalkenes.
A commercially available tantalum catalyst for the highly regioselective intermolecular hydroaminoalkylation of styrenes
Doerfler, Jaika,Doye, Sven
, p. 2790 - 2797 (2014/05/06)
The C-C bond-forming catalytic hydroaminoalkylation of terminal alkenes or styrenes enables a direct and 100 % atom-efficient synthesis of amines and can generally result in the formation of two regioisomers, the branched and the linear product. Herein, we report that high-yielding intermolecular hydroaminoalkylation reactions of styrenes can be achieved with excellent regioselectivities in the presence of the commercially available homoleptic catalyst pentakis(dimethylamino)tantalum. In all cases, the branched regioisomer is formed almost exclusively. Highly regioselective intermolecular hydroaminoalkylation reactions of styrenes are achieved in the presence of the commercially available homoleptic catalyst [Ta(NMe2)5]. The process activates the α-C-H bonds of N-methylanilines and 1,2,3,4-tetrahydroquinoline and gives access to the corresponding branched hydroaminoalkylation products in good-to-excellent yields. Copyright
A 2,6-bis(phenylamino)pyridinato titanium catalyst for the highly regioselective hydroaminoalkylation of styrenes and 1,3-butadienes
Doerfler, Jaika,Preuss, Till,Schischko, Alexandra,Schmidtmann, Marc,Doye, Sven
, p. 7918 - 7922 (2014/08/05)
The C-C bond forming catalytic hydroaminoalkylation of terminal alkenes, 1,3-dienes, or styrenes allows a direct and highly atom efficient (100 %) synthesis of amines which can result in the formation of two regioisomers, the linear and the branched product. We present a new titanium catalyst with 2,6-bis(phenylamino)pyridinato ligands for intermolecular hydroaminoalkylation reactions of styrenes and 1-phenyl-1,3-butadienes that delivers the corresponding linear hydroaminoalkylation products with excellent regioselectivities. Linear progress: A new Ti complex with 2,6-bis(phenylamino) pyridinato ligands catalyzes highly regioselective hydroaminoalkylation reactions of styrenes. The process that directly gives access to the corresponding linear hydroaminoalkylation products offers a new and flexible synthetic approach towards pharmaceutically important 3-arylpropylamines. It is also possible to convert (E)-1-phenyl-1,3-butadienes into the corresponding linear products.
