107909-63-7Relevant academic research and scientific papers
Efficient Synthesis of Amines by Iron-Catalyzed C=N Transfer Hydrogenation and C=O Reductive Amination
Facchini, Sofia Vailati,Cettolin, Mattia,Bai, Xishan,Casamassima, Giuseppe,Pignataro, Luca,Gennari, Cesare,Piarulli, Umberto
supporting information, p. 1054 - 1059 (2018/01/27)
Here we report the catalytic transfer hydrogenation (CTH) of non-activated imines promoted by a Fe-catalyst in the absence of Lewis acid co-catalysts. Use of the (cyclopentadienone)iron complex 1, which is much more active than the classical ‘Kn?lker complex’ 2, allowed to reduce a number of N-aryl and N-alkyl imines in very good yields using iPrOH as hydrogen source. The reaction proceeds with relatively low catalyst loading (0.5–2 mol%) and, remarkably, its scope includes also ketimines, whose reduction with a Fe-complex as the only catalyst has little precedents. Based on this methodology, we developed a one-pot CTH protocol for the reductive amination of aldehydes/ketones, which provides access to secondary amines in high yield without the need to isolate imine intermediates. (Figure presented.).
A highly-active and poison-tolerant Pt12 sub-nanocluster catalyst for the reductive amination of aldehydes with amines
Takahashi, Masaki,Imaoka, Takane,Hongo, Yushi,Yamamoto, Kimihisa
supporting information, p. 15919 - 15921 (2013/11/19)
A one-atom controlled platinum sub-nanocluster (under 1 nm) was synthesized using a phenylazomethine dendrimer template. This sub-nanocluster (SNC) catalyst exhibits a remarkable catalytic activity during reductive amination compared to the standard plati
Hydrogen-transfer reductive amination of aldehydes catalysed by nickel nanoparticles
Alonso, Francisco,Riente, Paola,Yus, Miguel
experimental part, p. 1289 - 1292 (2009/04/06)
Nickel nanoparticles have been found to catalyse the reductive amination of aldehydes by transfer hydrogenation with isopropanol at 76°C. Georg Thieme Verlag Stuttgart.
A novel, chemically robust, amine releasing linker
Kay, Corinne,Murray, Peter John,Sandow, Lisa,Holmes, Andrew B.
, p. 6941 - 6944 (2007/10/03)
A polymer supported sulfonamide 1, based on an amine protective group, has been developed as a novel linker for solid phase organic synthesis. The linker permits the immobilisation of alcohol substrates, and releases N-protected amines under mild nucleophilic cleavage conditions.
Free-Radical Chemistry of Imines
Tomaszewski, Miroslaw J.,Warkentin, John,Werstiuk, Nick H.
, p. 291 - 322 (2007/10/02)
Aryl radicals bearing an aldimino functional group as part of an ortho substituent cyclized by addition to C and/or N of the imino group.When the choice was between 5-exo closure to C and 6-endo closure to N, the former predominated.However, 6-endo closure to C predominated over 5-exo cyclization to N in isomeric imines.Absolute values of cyclization rate constants were determined and an explanation for the unusual 6-endo preference is offered.Chiral induction in 6-endo cyclization to C of an aldimine from D-glyceraldehyde acetonide was observed, and its sense was determined.
Lithium Alkylamide-Catalyzed Addition Reaction of Alkylamines to Vinyl Monomers. III. Addition Reaction of p-Substituted Benzylamines to Styrene and Divinylbenzenes
Hamana, Hiroshi,Iwasaki, Fuminori,Nagashima, Hiroyoshi,Hattori, Kazuhisa,Hagiwara, Tokio,Narita, Tadashi
, p. 1109 - 1113 (2007/10/02)
The lithium alkylamide-catalyzed addition reaction of p-substituted benzyamines with m- and p-divinylbenzene was examined in order to synthesize new styrene derivatives.Though divinylbenzene possesses two vinyl groups, 1:1 adducts, the N-(p-substituted benzyl)vinylphenethylamines (6, 8) were found to be prepared selectively.The reaction with styrene was also examined as a model reaction.From kinetic studies, the Hammett ρ values for the addition reaction of p-substituted benzylamines to the styrene, m-divinylbenzene and p-divinylbenzene, were -0.72, -0.67, and -1.1, respectively, at 50 deg C.
Electrochemical Reductive Alkylation of Azomethines with 1-Bromadamantane and 9-Bromo-tetrahydro-exo-dicyclopentadiene
Hess, U.,Lieberenz, C.,Feuerherd, B.
, p. 7 - 20 (2007/10/02)
Electrochemically generated radical anions of Schiffbases 1a-11 react in DMF and in the presence of bridgeheadhalogenides as 1-bromoadamantane and 9-bromo-tetrahydro-exo-dicyclopentadiene to 1--adamantanes and the correspondent 9-tetrahydro-exo-dicyclopentadienes.In the course of SET-mechanism originating bridgehead radicals couple with the azomethine-radicalanions at the position of the highest unpaired electron density, which is predominantly the carbon of the C,N-double bond.Only in cases when this density at the N-atom is relatively high, or steric hindrance impedes C-alkylation, N-hydroalkylated products as N,N-disubstituted 1-aminoadamantanes and 9-amino-tetrahydro-exo-dicyclopentadienes are formed.Product distribution, cyclic-voltammetric results and quantumchemical data are discussed in terms of mechanism.
