Categories: CN Bond Formation >
Synthesis of nitriles
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Recent Literature
A facile nickel-catalyzed oxidation of primary alcohols with
tetrabutylammonium peroxydisulfate in the presence of ammonium hydrogen
carbonate under basic aqueous conditions provides access to various aliphatic, aromatic and heterocyclic nitriles in excellent yields with very high purity.
F.-E. Chen, Y.-Y. Li, M. Xu, H.-Q. Jia, Synthesis,
2002, 1804-1806.
Various primary alcohols, and primary, secondary, and tertiary amines were
efficiently converted into the corresponding nitriles in good yields by
oxidation with 1,3-diiodo-5,5-dimethylhydantoin (DIH) in aqueous ammonia at 60
°C.
S. Iida, H. Togo, Synlett, 2007,
407-410.
S. Iida, H. Togo, Synlett, 2007,
407-410.
An efficient and highly selective method for the oxidative conversion of
primary amines to the corresponding nitriles using trichloroisocyanuric acid
in the presence of catalytic TEMPO provides a new entry to the synthesis of
various aliphatic, aromatic and heterocyclic nitriles in excellent yield.
F.-E. Chen, Y.-Y. Kuang, H.-F. Dai, L. Lu, M. Huo, Synthesis, 2003, 2629-2631.
Ruthenium supported on alumina acts as an efficient heterogeneous catalyst for
the
oxidation of non-activated as well as activated amines to the corresponding nitriles or imines with 1 atm of
dioxygen or air.
K. Yamaguchi, N. Mizuno, Angew. Chem. Int. Ed., 2003, 42,
1480-1483.
Among the reported examples of new reactivity of the hypervalent iodine
reagent DMP (Dess-Martin periodinane) are the one-step oxidation of
secondary amides to imides and N-acyl vinylogous carbamates or ureas
and the direct oxidation of benzylic and related primary amines to the
corresponding nitriles.
K. C. Nicolaou, C. J. N. Mathison, Angew. Chem., 2005, 117, 6146-6151.
An ethyl dichlorophosphate/DBU-mediated dehydration of aldoxime intermediates
from aldehydes enables a new and efficient one-pot conversion of various
aldehydes into the corresponding nitriles under mild reaction conditions.
J.-L. Zhu, F.-Y. Lee, J.-D. Wu, C.-W. Kuo, K.-S. Shia, Synlett, 2007,
1317-1319.
Graphite promotes the conversion of aldehydes into nitriles in high yields.
H. Shargi, M. H. Sarvari, Synthesis, 2003, 243-246.
H. Shargi, M. H. Sarvari, Synthesis, 2003, 243-246.
Different ketoximes, which are
prepared from the corresponding ketones, undergo the Beckmann rearrangement
at room temperature in excellent yields upon treatment with
2,4,6-trichloro[1,3,5]triazine in N,N-dimethylformamide. Nitriles are
obtained from aldoximes using the same procedure.
L. De Luca, G. Giacomelli, A. Porcheddu, J. Org.
Chem., 2002, 67, 6272-6274.
Adsorbed [RuCl2(p-cymene)]2
on activated carbon is an efficient, environmentally attractive and highly
selective catalyst for use in aerobic oxidations, hydrolytic oxidations and
dehydrations. The heterogeneous catalyst was recovered quantitatively by simple
filtration and could be reused with minimal loss of activity.
E. Choi, C. Lee, Y. Na, S. Chang, Org. Lett., 2002, 4,
2369-2371.
Various ketoximes undergo the Beckmann rearrangement when heated with
0.5 molar equiv. of chloral (hydrate) in the
absence of solvents and acids. Yields of the corresponding amides
were excellent after a simple work-up. Aromatic aldoximes were dehydrated to the
corresponding nitriles in excellent yields under similar conditions.
S. Chandrasekhar, K. Gopalaiah, Tetrahedron Lett.,
2003, 44, 755-756.
A convenient, environmentally friendly method for the synthesis of optically
active aldoximes and nitriles starting from chiral nitroalkanes was
developed.
C. Czekelius, E. M. Carreira, Angew. Chem., 2005, 117, 618-621.
