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. Int. Ed., 2005, 44, 5992-5997.

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 novel and facile transformation of N,N-disubstituted glycylamides into corresponding cyanamides using pentavalent iodine reagents and tetraethylammonium bromide offers advantages such as use of non toxic reagents, shorter reaction times and good yields.
K. H. Chaudhari, U. S. Mahajan, D. S. Bhalerao, K. G. Akamanchi, Synlett, 2007, 2815-2818.

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. Int. Ed., 2005, 44, 612-615.