Hydroaminomethylation with novel rhodium-carbene complexes: an efficient catalytic approach to pharmaceuticals.
Starting from [{Rh(cod)Cl}(2)] and 1,3-dimesitylimidazole-2-ylidenes the novel [RhCl(cod)(carbene)] complexes 1-5 have been synthesized, characterized, and tested in the hydroaminomethylation of aromatic olefins. The influence of different ligands and reaction parameters on the catalytic activity was investigated in detail applying 1,1-diphenylethylene and piperidine as a model system. The scope and limitations of the novel catalysts is shown in the preparation of 16 biologically active 1-amino-3,3-diarylpropenes. In general, high chemo- and regioselectivity as well as good yields of the desired products were achieved.
Ahmed
Moballigh
M
Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany.
Buch
Cathleen
C
Routaboul
Lucie
L
Jackstell
Ralf
R
Klein
Holger
H
Spannenberg
Anke
A
Beller
Matthias
M
D000475:Alkenes / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D006838:Hydrocarbons / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry; D008024:Ligands; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008745:Methylation; D008956:Models, Chemical; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D004364:Pharmaceutical Preparations / Q000138:chemical synthesis*; D010880:Piperidines / Q000737:chemistry; D011407:Propane / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D012238:Rhodium / Q000737:chemistry*; D013343:Styrenes / Q000737:chemistry
D000475:Alkenes; D000588:Amines; D006838:Hydrocarbons; D007093:Imidazoles; D008024:Ligands; D009942:Organometallic Compounds; D004364:Pharmaceutical Preparations; D010880:Piperidines; D013343:Styrenes; C030011:carbene; C032727:piperidine; C007518:1,1-diphenylethylene; D012238:Rhodium; D008697:Methane; D011407:Propane