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.
A simple and efficient one-pot, three-component Strecker reaction of aldehydes
and ketones with aliphatic or aromatic amines and trimethylsilyl cyanide in the
presence of a palladium Lewis acid catalyst allows the synthesis of
α-aminonitriles in good yields at room temperature.
J. Jarusiewicz, Y. Choe, K. Soo. Yoo, C. P. Park, K. W. Jung, J. Org. Chem., 2009,
74, 2873-2876.
A highly enantioselective cyanation of imines at room temperature in the
presence of 5 mol% of a partially hydrolyzed titanium alkoxide (PHTA)
precatalyst together with a readily available N-salicyl-β-aminoalcohol
ligand gives aminonitriles with up to 98% ee and quantitative yields in 15 min
of reaction time. Various N-protecting groups are tolerated.
A. M. Seayad, B. Ramalingam, K. Yushinaga, T. Nagata, C. L. L. Chai, Org. Lett., 2010,
12, 264-267.
An aluminum complex was found to be high yielding and enantioselective for
the addition of cyanide to aldimines and ketimines. The present catalyst
provides uniformly high enantioselectivity for aromatic, heteroaromatic, and
aliphatic aldimines and ketimines using ethyl cyanoformate as the cyanide source.
J. P. Abell, H. Yamamoto, J. Am. Chem. Soc., 2009,
131, 15118-15119.
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.
