Categories: C-C Bond Formation > Nitrogen-containing molecules >
Synthesis of α-Aminonitriles
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Name Reactions
Recent Literature
RuCl3-catalyzed oxidative cyanation of tertiary amines with sodium
cyanide under molecular oxygen at 60°C gives the corresponding α-aminonitriles
in excellent yields. This reaction is clean and should be an environmentally
benign and useful process.
S.-I. Murahashi, N. Komiya, H. Terai, T. Nakae, J. Am. Chem. Soc.,
2003,
125, 15312-15313.
A novel, simple and efficient one-pot synthesis of α-aminonitriles has been
achieved by a three-component condensation of carbonyl compounds, amines and
trimethylsilyl cyanide in the presence of (bromodimethyl)sulfonium bromide
as a catalyst at room temperature.
B. Das, R. Ramu, B. Ravikanth, K. Ravinder Reddy,
Synthesis, 2006, 1419-1422.
An environmentally benign and highly efficient, biomimetic procedure for the
nucleophilic addition of trimethylsilyl cyanide to imines (Strecker reaction)
using β-cyclodextrin as a catalyst and water as solvent afforded
α-aminonitriles in quantitative
yields. The catalyst can be recycled a number of times without loss in activity.
K. Surendra, N. S. Krishnaveni, A. Mahesh, K. R. Rao, J. Org. Chem., 2006,
71, 2532-2534.
A very fast, simple one-step, environmentally friendly procedure for the synthesis
of α-aminonitriles in high yields from aldehydes, using trimethylsilyl cyanide in
the absence of solvent, gives almost quantitative yields of
the corresponding α-aminonitriles. However, only
cyclic ketones afford the corresponding α-aminonitriles in excellent chemical
yields.
A. Baeza, C. Nájera, J. M. Sansano, Synthesis, 2007,
1230-1234.
An N-heterocyclic carbene as a nucleophilic organocatalyst allows the
cyanation of ketones and ketimines with TMSCN in good yields under mild
reaction conditions.
Y. Fukuda, K. Kondo, T. Aoyama,
Synthesis, 2006, 2649-2652.
Aryl imines, formed in situ from aldehydes and amines undergo mild nucleophilic addition with trimethylsilyl cyanide on the surface of montmorillonite KSF clay to afford the corresponding α-aminonitriles in excellent yields. The solid acid can be recovered and recycled in subsequent reactions with a gradual decrease of activity.
J. S. Yadav, B. V. S. Reddy, B. Eeshwaraiah, M. Srinivas, Tetrahedron,
2004, 60, 1767-1771.
