2726
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8. Ramón, R. S.; Bosson, J.; Díez-González, S.; Marion, N.; Nolan, S. P. J. Org. Chem.
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to excellent isolated yields. The switch from an expensive metal
catalyst provides another example of using a ‘cheap metal for a no-
ble task’.19
9. Ali, M. A.; Punniyamurthy, T. Adv. Synth. Catal. 2010, 352, 288.
10. Kim, S. E.; Lee, H. S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2010, 51, 1589.
11. Mishra, A.; Ali, A.; Upreti, S.; Gupta, R. Inorg. Chem. 2008, 47, 154.
12. Li, Z.; Ding, R.; Lu, Z.; Xiao, S.; Ma, X. J. Mol. Catal. A 2006, 250, 100.
13. In(NO3)3 is over 50Â cheaper than Ru(PPh3)3(CO)H2 and over 150Â cheaper
than [Ir(Cp*)Cl2]2. However, In(NO3)3 is still almost 1000Â more expensive
than ZnCl2.
14. Zinc oxide (2 equiv) has been reported to catalyze the Beckmann
rearrangement of ketones and aldehydes: Sharghi, H.; Hosseini, M. Synthesis
2002, 1057.
Acknowledgement
We thank the EPSRC for the award of a studentship (to C.L.A).
Supplementary data
15. Capello, C.; Fischer, U.; Hungerbühler, K. Green Chem. 2007, 9, 927.
16. For methods of converting aldoximes into nitriles, see: (a) Yang, S. H.; Sukbok,
C. Org. Lett. 2001, 3, 4209; (b) Kim, H. S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett.
2009, 50, 1717. and references therein; (c) Kim, E. S.; Kim, H. S.; Kim, J. N.
Tetrahedron Lett. 2009, 50, 2973; (d) Yadav, L. D. S.; Srivastava, V. P.; Patel, R.
Tetrahedron Lett. 2009, 50, 5532.
17. For methods of converting aldehydes into primary amides, see: (a) Gilman,
N. W. Chem. Commun. 1971, 733; (b) Sharghi, H.; Sarvari, M. H.
Tetrahedron 2002, 58, 10323; (c) Shie, J.-J.; Fang, J.-M. J. Org. Chem.
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Org. Chem. 2006, 71, 3149.
18. For methods of converting aldehydes into nitriles, see: (a) Kumar, H. M. S.;
Reddy, S.; Reddy, P. T.; Yadav, J. S. Synthesis 1999, 586; (b) Bajpai, A. R.;
Deshpande, A. B.; Samant, S. D. Synth. Commun. 2000, 30, 2785; (c) Ballini, R.;
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Synth. Commun. 2006, 36, 1347; (e) Zhu, J.-L.; Lee, F.-Y.; Wu, J.-D.; Kuo, C.-W.;
Shia, K.-S. Synlett 2007, 1317; (f) Khezri, S. H.; Azimi, N.; Mohammed-Vali, M.;
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Supplementary data associated with this article can be found, in
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