Aryl nitriles have been prepared in good yields from the corresponding aryl halides with potassium hexacyanoferrate(II) using CuI/1,10-phenanthroline as the catalyst system. Furthermore, the reaction is compatible with a wide range of functional groups including nitro and carbonyl substituents.
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(a) LabrockR.C., Comprehensive Organic Transformations; VCH: New York, 1989. pp 819–995; (b) K.W. Rosenmund and E. Struck, Berichte, 1919, 52, 1749.
3.
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4.
For the palladium-catalysed cyanation of aryl halides, see: (a) JinF., and ConfaloneP.N., Tetrahedron Lett., 2000, 41, 3271; (b) M. Sundermeier, A. Zapf and M. Beller, Eur. J. Inorg. Chem., 2003, 3513. and references cited therein; (c) A. Zhang and J.L. Neumeyer, Org. Lett., 2003, 5, 201; (d) R. Chidambaram, Tetrahedron Lett., 2004, 45, 1441; (e) K.M. Marcantonio, L.F. Frey, Y. Liu, Y. Chen, J. Strine, B. Phenix, D.J. Wallace and C.Y. Chen, Org. Lett., 2004, 6, 3723; (f) S.E. Collibee and R.R. Strivastava, Tetrahedron Lett., 2004, 45, 8895; (g) T. Schareina, A. Zapf and M. Beller, Chem. Commun., 2004, 1388; (h) J.M. Williams and C.Y. Yang, Org. Lett., 2004, 6, 2837; (i) T. Schareina, A. Zapf and M. Beller, J. Organomet. Chem., 2004, 689, 4576; (j) F. Stazi, G. Palmisano, M. Turconi and M. Stantagostino, Tetrahedron Lett, 2005, 46, 1815; (k) M. Hatsuda and M. Seki, Tetrahedron, 2005, 61, 9908; (l) M.L. Jensen, A.S. Gajare, K. Toyota, M. Yoshijuji and F. Ozawa, Tetrahedron Lett, 2005, 46, 8645; (m) L.S. Lin, B.P. Fors and H.R. Chobanian, Tetrahedron Lett., 2006, 47, 3303; (n) J. Whittall, P.M. Cormack and W.R. Pitts, Tetrahedron, 2006, 62, 4705; (o) D. Gelman and O. Grossman, Org. Lett., 2006, 8, 1189; (p) L.-H. Li, Z.-L. Pan and Y.-M. Liang, Synlett, 2006, 2094; (q) T. Schareina, A. Zapf, W. Magerlein, N. Muller and M. Beller, Tetrahedron Lett., 2007, 48, 1087; (r) Y.-N. Cheng, Z. Duan, T. Li and Y.-J. Wu, Synlett, 2007, 543.
5.
For the nickel-catalysed cyanation of aryl halides, see: (a) CassarL., J. Organomet. Chem., 1973, 54, 57; (b) L. Cassar, M. Foà, F. Montanari and G.P. Marinelli, J. Organomet. Chem., 1979, 173, 335; (c) Y. Sakaibara, F. Okuda, A. Shimoyabashi, K. Kirino, M. Sakai, N. Uchino and K. Takagi, Bull. Chem. Soc. Jpn., 1988, 61, 1985; (d) Y. Sakaibara, F. Okuda, A. Shimoyabashi, Y. Ido, K. Sakai, M. Sakai and N. Uchino, Bull. Chem. Soc. Jpn., 1993, 66, 2776; (e) V. Percec, J.-Y. Bae, and D.H. Hill, J. Org. Chem., 1995, 60, 6895; (f) N.E. Leadbeater and R.K. Arvela, J. Org. Chem., 2003, 68, 9122.
6.
SchareinaT., ZapfA., and BellerM., Tetrahedron Lett., 2005, 46, 2585.
7.
SchareinaT., ZapfA., MagerleinW., MullerN., and BellerM., Synlett, 2007, 555.
8.
(a) CristauH.-J., OualiA., SpindlerJ.-F., and TailleferM., Chem. Eur. J., 2005, 11, 2483; (b) M. Kuil, L. Bekedam, G.M. Visser, A. van den Hoogenband, J.W. Terpstra, P.C.J. Kamer, P.W.N.M. Kamer van Leeuwen and G.P.F. van Strijdonck, TetrahedronLett., 2005, 46, 2405; (c) R.A. Altman and S.L. Buchwald, Org. Lett., 2006, 8, 2779.
9.
K4[Fe(CN)6]·3H2O is ground to a fine powder and dried under a high vacuum at 80°C overnight.
