amination
Reactions
=Aminase enzymes=
Enzymes that catalyse this reaction are termed aminases. Amination can occur in a number of ways including reaction with ammonia or another amine such as an alkylation, reductive amination and the Mannich reaction.
=Acid-catalysed hydroamination=
Many alkyl amines are produced industrially by the amination of alcohols using ammonia in the presence of solid acid catalysts. Illustrative is the production of tert-butylamine:
:NH3 + CH2=C(CH3)2 → H2NC(CH3)3
The Ritter reaction of isobutene with hydrogen cyanide is not useful in this case because it produces too much waste.{{Ullmann|doi=10.1002/14356007.a02_001|title=Amines, Aliphatic|year=2000|last1= Eller|first1=Karsten|last2=Henkes|first2=Erhard|last3=Rossbacher|first3=Roland|last4=Höke|first4=Hartmut|isbn=3527306730}}
= Electrophilic amination =
Usually, the amine reacts as the nucleophile with another organic compound acting as the electrophile. This sense of reactivity may be reversed for some electron-deficient amines, including oxaziridines, hydroxylamines, oximes, and other N–O substrates. When the amine is used as an electrophile, the reaction is called electrophilic amination. Electron-rich organic substrates that may be used as nucleophiles for this process include carbanions and enolates.
=Miscellaneous methods=
Alpha hydroxy acids can be converted into amino acids directly using aqueous ammonia solution, hydrogen gas and a heterogeneous metallic ruthenium catalyst. Deng, Weiping, et al. "Catalytic amino acid production from biomass-derived intermediates." Proceedings of the National Academy of Sciences 115.20 (2018): 5093-5098. {{doi|10.1073/pnas.1800272115}}
=Metal-catalyzed hydroamination=
In hydroamination, amines add to alkenes.Liangbin Huang, Matthias Arndt, Käthe Gooßen, Heinrich Heydt, and Lukas J. Gooßen "Late Transition Metal-Catalyzed Hydroamination and Hydroamidation" Chem. Rev., 2015, 115 (7), pp 2596–2697. {{doi|10.1021/cr300389u}} When substituted amines add, the result is alkene carboamination.
See also
- Alkylation, the addition of an alkyl group
- Acylation, the addition of an acyl group (-C(O)R)
- Deamination
References
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