Categories: C-C Bond Formation > Nitrogen-containing molecules >
Synthesis of Nitriles (cyanation)
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Name Reactions
Recent Literature
Nucleophilic fluorination using CsF or alkali metal fluorides was completed in
short reaction time in the presence of [bmim][BF4] affording the
desired products without any byproducts. Facile nucleophilic substitutions such
as halogenations, acetoxylation, nitrilation, and alkoxylations in the presence
of ionic liquids provided the desired products in good yields.
D. W. Kim, C. E. Song, D. Y. Chi, J. Org. Chem.,
2003, 68, 4281-4285.
Hydroboration with catecholborane, followed by treatment with easily
available reagents such as alkenyl sulfones or alkynyl phenyl sulfones in
the presence of a radical initiator, represents an effective and simple
one-pot procedure for direct vinylation, formylation, and cyanation.
A.-P. Schaffner, V. Darmency, P. Renaud, Angew. Chem. Int. Ed.,
2006,
45, 5847-5849.
A
direct cyanation of benzylic alcohols with TMSCN under the catalysis of
5-10 mol % of InBr3 allows the synthesis of the corresponding
nitriles in short reaction time with good yields.
G. Chen, Z. Wang, J. Wu, K. Ding, Org. Lett.,
2008,
10, 4573-4576.
Gd(OTf)3 as co-catalyst dramatically accelerated a Ni-catalyzed
conjugate addition of cyanide to enones. The substrate scope of the reaction is
broad, including cyclic, linear, branched, and aromatic enones. Gadolinium
triflate is supposed to facilitate the oxidative addition of Ni(0) to enones,
which constitutes a key step in the catalytic cycle.
Y. Tanaka, M. Kanai, M. Shibasaki, Synlett, 2008, 2295-2298.
A (Salen)Al-Cl complex catalyzes the asymmetric conjugate addition of
hydrogen cyanide to α,β-unsaturated imides in high yields and
enantioselectivities. The cyanide adducts can readily be converted into a
variety of useful chiral building blocks, including α-substituted-β-amino
acids.
G. M. Sammis, E. N. Jacobsen, J. Am. Chem. Soc., 2003,
125, 4442-4443.
A clean and efficient method for the oxidative transformations of primary
carboxamides to one-carbon dehomologated nitriles using the combination of
o-iodoxybenzoic acid and tetraethylammonium bromide exhibits a broad scope and
is expected to be of great utility in organic synthesis.
D. S. Bhalarao, U. S. Mahajan, K. H. Chaudhari, K. G. Akamanchi, J. Org. Chem., 2007,
72, 662-665.
