1039968-13-2Relevant articles and documents
NEW METHOD FOR THE SYNTHESIS OF UNSYMMETRICAL TERTIARY AMINES
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Paragraph 0090, (2020/08/25)
Disclosed is a new method for the synthesis of unsymmetrical tertiary amines using alcohol and an imine, and to new tertiary amines.
Phosphine-Free Well-Defined Mn(I) Complex-Catalyzed Synthesis of Amine, Imine, and 2,3-Dihydro-1 H-perimidine via Hydrogen Autotransfer or Acceptorless Dehydrogenative Coupling of Amine and Alcohol
Das, Kalicharan,Mondal, Avijit,Pal, Debjyoti,Srivastava, Hemant Kumar,Srimani, Dipankar
supporting information, p. 1815 - 1825 (2019/04/30)
The application of nontoxic, earth-abundant transition metals in place of costly noble metals is a paramount goal in catalysis and is especially interesting if the air- and moisture-stable ligand scaffold is used. Herein, we report the synthesis of amines/imines directly from alcohol and amines via hydrogen autotransfer or acceptorless dehydrogenation catalyzed by well-defined phosphine-free Mn complexes. Both imines and amines can be obtained from the same set of alcohols and amines using the same catalyst, only by tuning the reaction conditions. The amount and nature of the base are found to be a highly important aspect for the observed selectivity. Both the primary and secondary amines have been employed as substrates for the N-alkylation reaction. As a highlight, we showed the chemoselective synthesis of resveratrol derivatives. Furthermore, the Mn-catalyzed dehydrogenative synthesis of structurally important 2,3-dihydro-1H-perimidines has also been demonstrated. Density functional theory calculations were also carried out to model the reaction path and to calculate the reaction profile.
Selective reductive amination of aldehydes from nitro compounds catalyzed by molybdenum sulfide clusters
Pedrajas,Sorribes,Junge,Beller,Llusar
supporting information, p. 3764 - 3768 (2017/08/21)
Secondary amines are selectively obtained from low value starting materials using hydrogen and a non-noble metal-based catalyst. The reductive amination of aldehydes from nitroarenes or nitroalkanes is efficiently catalyzed by a well-defined diamino molybdenum sulfide cluster in a one-pot homogeneous reaction. The integrity of the molecular cluster catalyst is preserved along the process.
Cobalt(II) phthalocyanine-catalyzed highly chemoselective reductive amination of carbonyl compounds in a green solvent
Kumar, Vishal,Sharma, Upendra,Verma, Praveen K.,Kumar, Neeraj,Singh, Bikram
supporting information; experimental part, p. 870 - 878 (2012/05/04)
Cobalt phthalocyanine has been employed for the highly chemoselective reductive amination of aldehydes and ketones in ethanol as a green solvent. A large range of functional groups such as nitro, acid, amide, ester, nitrile, halogen, lactone, methoxy, hydroxy, alkene, N-benzyl, O-benzyl and heterocyclic rings were well tolerated under the present reaction conditions. Copyright
Multisite solid (NHC)NN-Ru-catalysts for cascade reactions: Synthesis of secondary amines from nitro compounds
Del Pozo, Carolina,Corma, Avelino,Iglesias, Marta,Sanchez, Felix
experimental part, p. 110 - 116 (2012/08/08)
Supported ruthenium complexes based on electron-rich (NHC)NN-pincer-type ligands selectively catalyze the formation of substituted amines from nitroaromatics and carbonyl compounds through a series of consecutive steps which involves the reduction of nitro group to amine, the formation of an imine or iminium ion intermediate, followed by in situ reduction to an alkylated amine of higher order in a single operation. Solid complexes result active and recyclable catalysts and no deactivation was observed after repeated recycling.
Efficient and highly chemoselective direct reductive animation of aldehydes using the system silane/oxorhenium complexes
Sousa, Sara C. A.,Fernandes, Ana C.
experimental part, p. 2218 - 2226 (2010/11/05)
This work reports a novel method for direct reductive amination of aldehydes with silanes catalyzed by several high-valent oxorhenium(V) and oxorhenium (VII) complexes. The catalytic system PhSiH3/ReIO 2(PPh3)2 (2.5mol%) was very efficient for the synthesis of secondary amines and highly chemoselective, tolerating a wide range of functional groups such as -NO2, -CF3, -SO 2R, -CO2R, -F, -Cl, -Br, -I, -CN, -OH, -OCH3, -SCH3, NCOR, and double bonds. This novel method was also employed in the synthesis of tertiary amines with moderate yields.
