One-Pot Synthesis of Symmetrical Tertiary and Secondary Amines from Carbonyl Compounds, Ammonium Carbonate and Carbon Monoxide as a Reductant
Rh-catalyzed one-step synthesis of tertiary and secondary amines from aldehydes and ketones, ammonium carbonate serving as nitrogen source, and carbon monoxide as a reducing agent has been developed. Aliphatic and aromatic aldehydes lead to the corresponding tertiary symmetrical amines in 69–83 % yields. Aromatic and aliphatic ketones lead to the corresponding secondary symmetrical amines which were obtained in 62–79 % yields.
Colloid and nanosized catalysts in organic synthesis: XII. Hydrogenation of carbonitriles catalyzed by nickel nanoparticles
Hydrogenation of carbonitriles catalyzed by nickel nanoparticles in isopropanol proceeds under atmospheric pressure of hydrogen within 6-15 h to yield mainly secondary amines. Hydrogenation of α-aminonitriles results in reductive decyanation. β-Aminonitriles undergo hydrogenolysis at the nitrogen-carbon bond.
Mokhov,Popov,Shcherbakova
p. 273 - 280
(2016/04/20)
An efficient synthesis of tertiary amines from nitriles in aprotic solvents
Tertiary amines are utilized extensively as non-nucleophilic proton scavengers for a number of organic transformations. Herein we report the efficient syntheses of tertiary alkyl amines from their corresponding alkyl nitriles in the presence of a heterogeneous palladium catalyst and a source of dihydrogen in aprotic solvents. The reaction is atom economic, the conditions are mild, and the isolated yields are virtually quantitative. The degree of amine alkylation shows some solvent dependency; in polar protic solvents such as ethanol or methanol, the reaction affords a mixture of products with the secondary alkyl amine as the major product.
Shares, Jonathan,Yehl, Jenna,Kowalsick, Amanda,Byers, Philip,Haaf, Michael P.
experimental part
p. 4426 - 4428
(2012/09/25)
REDUCTIVE AMINATION OF ALIPHATIC ALDEHYDES IN THE PRESENCE OF GROUP-VIII METALS
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Smaeva, T. P.,Yakushkin, M. I.,Dobrotvorskii, A. M.
p. 1221 - 1225
(2007/10/02)
REDUCTIVE AMINATION OF ISOBUTYRALDEHYDE TO ISOBUTYLAMINES IN PRESENCE OF VARIOUS HYDROGENATION CATALYSTS
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Smaeva, T. P.,Yakushin, M. I.,Akulova, N. G.,Bazyleva, R. V.,Lebedeva, N. V.
p. 1039 - 1043
(2007/10/02)
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