Categories: C-C Bond Formation > Arenes >
Cyanations
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Recent Literatur
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 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.
