Categories: C-C Bond Formation > Arenes >
Cyanations
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Recent Literatur
Various electron-rich aromatics could be smoothly converted into the
corresponding aromatic nitriles in good yields by treatment with POCl3
and DMF, followed by molecular iodine in aqueous ammonia. The present reaction
is a novel metal-free one-pot method for the preparation of aromatic nitriles
from electron-rich aromatics.
S. Ushijima, H. Togo, Synlett, 2010,
1067-1070.
In the presence of a highly effective Pd/CM-phos catalyst, an efficient
cyanation of aryl chlorides proceeds at 70°C in general. Common functional
groups such as keto, aldehyde, ester, nitrile and -NH2, and
heterocyclic coupling partners are well tolerated. Moreover, a sterically
hindered nonactivated ortho,ortho-disubstituted electrophile is shown to
be a feasible coupling partner in cyanation.
P. Y. Yeung, C. M. So, C. P. Lau, F. Y. Kwong, Org. Lett., 2011,
13, 648-651.
A trans-spanned palladium has efficiently and selectively catalyzed the
cyanation of aryl halides. The suggested reaction conditions are mild,
exhibit good scope of substrates, and circumvent the need for an inert
atmosphere and amine co-ligands.
O. Grossman, D. Gelman, Org. Lett.,
2006,
8, 1189-1191.
K4[Fe(CN)6] (a nontoxic cyanide source) allows in
combination with 0.1 mol % Pd(OAc)2 a practical, ligand-free
cyanation of aryl bromides in good to excellent yields.
S. A. Weissman, D. Zewge, C. Chen, J. Org. Chem., 2005,
70, 1508-1510.
A practical method for palladium-catalyzed cyanation of aryl halides using Pd/C
can be applied to various aryl bromide and active aryl chloride substrates to
effect efficient conversions. The process features many advantages over existing
cyanation conditions and the practical utility of the process has been
demonstrated on scale.
H. Yu, R. N. Richey, W. D. Miller, J. Xu, S. A. May, J. Org. Chem., 2011,
76, 665-668.
A palladium-catalyzed cyanation allows the conversion of highly challenging
electron-rich aryl chlorides, in addition to electron-neutral and
electron-deficient substrates, as well as nitrogen- and sulfur-containing
heteroaryl chlorides under relatively mild conditions in the presence of
sterically demanding, electron-rich phosphines as ligands.
A. Littke, M. Soumeillant, R. F. Kaltenbach III, R. J. Cherney, C. M. Tarby,
S. Kiau, Org. Lett., 2007,
9, 1711-1714.
An efficient, mild, and inexpensive copper-catalyzed domino halogen
exchange-cyanation procedure for aryl bromides was developed. The new method
represents a significant improvement over the traditional Rosenmund-von
Braun reaction: the use of catalytic amounts of copper and an apolar solvent
greatly simplifies the isolation and purification. In addition, the new
method exhibits excellent functional group compatibility.
J. Zanon, A. Klapars, S. L. Buchwald, J. Am. Chem. Soc., 2003,
125, 2890-2891.
Cyanation of aryl chlorides with potassium hexacyanoferrate(II) catalyzed by a
cyclopalladated ferrocenylimine tricyclohexylphosphine complex is applicable to
both activated and deactivated aryl chlorides. The corresponding aryl nitriles
were isolated in good yields.
Y.-n. Cheng, Z. Duan, T. Li, Y. Wu, Synlett, 2007, 543-546.
