161012-69-7Relevant academic research and scientific papers
Bifunctional (cyclopentadienone)iron-tricarbonyl complexes: Synthesis, computational studies and application in reductive amination
Moulin, Solenne,Dentel, Helene,Pagnoux-Ozherelyeva, Anastassiya,Gaillard, Sylvain,Poater, Albert,Cavallo, Luigi,Lohier, Jean-Francois,Renaud, Jean-Luc
supporting information, p. 17881 - 17890 (2014/01/17)
Reductive amination under hydrogen pressure is a valuable process in organic chemistry to access amine derivatives from aldehydes or ketones. Knoelker's complex has been shown to be an efficient iron catalyst in this reaction. To determine the influence of the substituents on the cyclopentadienone ancillary ligand, a series of modified Knoelker's complexes was synthesised and fully characterised. These complexes were also transformed into their analogous acetonitrile iron-dicarbonyl complexes. Catalytic activities of these complexes were evaluated and compared in a model reaction. The scope of this reaction is also reported. For mechanistic insights, deuterium-labelling experiments and DFT calculations were undertaken and are also presented. Festival of amination: Two series of modified Knoelker's complexes were synthesised and applied in the reductive amination of various carbonyl derivatives with primary or secondary amines (see scheme, TIPS = triisopropylsilyl). For a mechanistic insight, deuterium-labelling experiments and DFT calculations were undertaken and are also presented. Copyright
Kn?lker's iron complex: An efficient in situ generated catalyst for reductive amination of alkyl aldehydes and amines
Pagnoux-Ozherelyeva, Anastassiya,Pannetier, Nicolas,Mbaye, Mbaye Diagne,Gaillard, Sylvain,Renaud, Jean-Luc
supporting information; experimental part, p. 4976 - 4980 (2012/06/30)
An aminated series: A well-defined iron-catalyzed reductive amination reaction of aldehydes and ketones with aliphatic amines using molecular hydrogen is presented. Under mild conditions, good yields for a broad range of alkyl ketones as well as aldehydes were achieved. Copyright
A mild one-pot conversion of alkenes into amines through tandem ozonolysis and reductive amination
Kyasa, Shivakumar,Fisher, Thomas J.,Dussault, Patrick H.
experimental part, p. 3475 - 3481 (2011/12/04)
The selective reduction of hydroperoxyacetals to aldehydes by sodium triacetoxyborohydride provides the basis for a mild one-pot synthesis of amines from alkenes. Georg Thieme Verlag Stuttgart.
Preparation of secondary amines by reductive animation with metallic magnesium
Micovic, Ivan V.,Ivanovic,Roglic, Goran M.,Kiricojevic, Vesna D.,Popovic, Jelena B.
, p. 265 - 269 (2007/10/03)
A novel and efficient method for the preparation of secondary amines by reductive animation of carbonyl compounds with primary amines has been developed. The reduction, effected with metallic magnesium in methanol, utilizing triethylamine-acetic acid as a buffer, gave pure secondary amines, mostly in good yields (65-80%). No formation of tertiary amines or alcohols was observed. Use of ammonium acetate as an amino component gave primary amines in modest yields (ca. 50%), together with variable amounts of secondary amines. Enamines failed to undergo reduction. The method is inexpensive, relatively rapid, operationally simple and suitable for large-scale preparations. In addition, a simple method for separation of primary amines from secondary ones has been developed.
