A. Martínez-Asencio et al. / Tetrahedron 68 (2012) 3948e3951
3951
0
0006 and CTQ2011-24151) and the Generalitat Valenciana (G.V.;
11. (a) Park, S.; Choi, Y.-a.; Han, H.; Yang, S. H.; Chang, S. Chem. Commun. 2003,
936e1937; (b) Kim, M.; Lee, J.; Lee, H.-Y.; Chang, S. Adv. Synth. Catal. 2009, 351,
807e1812.
2. Leusink, A. J.; Meerbeek, T. G.; Noltes, J. G. Recl. Trav. Chim. Pay-Bas 1976, 95,
123e125.
3. Mishra, A.; Ali, A.; Upreti, S.; Gupta, R. Inorg. Chem. 2008, 47, 154e161.
4. Ram oꢀ n, R. S.; Bosson, J.; Díez-Gonz ꢀa lez, S.; Marion, N.; Nolan, S. P. J. Org. Chem.
010, 75, 1197e1202.
5. For a mechanistic study, see: Allen, C. L.; Lawerence, R.; Emmett, L.; Williams, J.
M. J. Adv. Synth. Catal. 2011, 353, 3262e3268.
6. The first direct conversion of aldehydes into primary amides catalyzed by Cu-
SO $5H O using hydroxylammonium chloride and bases was published during
1
1
PROMETEO 2009/03, FEDER). A.M.-A. thanks to the University of
Alicante for a fellowship. We gratefully acknowledge the polishing
of our English by Mrs. Oriana C. Townley.
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Supplementary data
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1
clude MOL files and InChIKeys of the most important compounds
described in this article.
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4
2
the preparation of this manuscript: Ganguly, N. C.; Roy, S.; Mondal, P. Tetra-
hedron Lett. 2012, 53, 1413e1416.
17. Allen, C. L.; Burel, C.; Williams, J. M. J. Tetrahedron Lett. 2010, 51, 2724e2726.
1
8. (a) Gnanamgari, D.; Crabtree, R. H. Organometallics 2009, 28, 922e924; (b) Hull,
J. F.; Hilton, S. T.; Crabtree, R. H. Inorg. Chim. Acta 2010, 363, 1243e1245.
References and notes
1
9. (a) Fujiwara, H.; Ogasawara, Y.; Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed.
2007, 46, 5202e5205; (b) Fujiwara, H.; Ogasawara, Y.; Kotani, M.; Yamaguchi,
K.; Mizuno, N. Chem. Asian J. 2008, 3, 1715e1721.
1
2
. Science of Synthesis; Weinreb, S. M., Ed.; Thieme: Stuttgart, 2005; Vol. 21.
. (a) Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Org. Biomol. Chem. 2006,
, 2337e2347; (b) Constable, D. J. C.; Dunn, P. J.; Hayler, J. D.; Humphrey, G. R.;
4
20. Ali, M. A.; Punniyamurthy, T. Adv. Synth. Catal. 2010, 352, 288e292.
oꢀ n, D. J.; Yus, M. Tetrahedron Lett. 2010, 51,
Leazer, J. L.; Linderman, R. J.; Lorenz, K.; Manley, J.; Pearlman, B. A.; Wells, A.;
Zaks, A.; Zhang, T. Y. Green. Chem. 2007, 9, 411e420.
21. (a) Martínez-Asencio, A.; Ram
325e327; (b) Martínez-Asencio, A.; Ram
3140e3149.
22. (a) Martínez, R.; Brand, G. J.; Ram
3683e3686; (b) Martínez, R.; Ram
oꢀ n, D. J.; Yus, M. Tetrahedron 2011, 67,
3. (a) Beckmann, E. Ber. Dtsch. Chem. Ges. 1886, 19, 988e993; (b) Donaruma, L. G.;
Heldt, W. Z. Org. React. 1960, 11, 1e156; (c) Gawley, R. E. Org. React. 1988, 35,
oꢀ n, D. J.; Yus, M. Tetrahedron Lett. 2005, 46,
oꢀ n, D. J.; Yus, M. Tetrahedron 2006, 62,
oꢀ n, D. J.; Yus, M. Tetrahedron 2006, 62,
oꢀ n, D. J.; Yus, M. Eur. J. Org. Chem. 2007,
1
e420.
. Izumi, Y.; Ichihashi, H.; Shimazu, Y.; Kitamura, M.; Sato, H. Bull. Chem. Soc. Jpn.
007, 80, 1280e1287.
. Smith, M. B.; March, J.; Advanced Organic Chemistry, 5th ed.; Wiley: New York,
001; Vol. 9, pp 1415e1416.
. Paul, R. Compt. Rend. 1937, 204, 363e365.
. Hoffenberg, D. S.; Hauser, C. R. J. Org. Chem. 1955, 20, 1496e1500.
. Field, L.; Hughmark, P. B.; Shumaker, S. H.; Marshall, W. S. J. Am. Chem. Soc. 1961,
3, 1983e1986.
. (a) Zhdanov, Y. A.; Alekseev, Y. E.; Sudareva, T. P. Dokl. Akad. Nauk 1978, 238,
80e582; Chem. Abstr. 1978, 88, 152880; (b) Marzino, N. C.; Ronchin, L.; Tortato,
4
5
6
8982e8987; (c) Martínez, R.; Ram
8988e9001; (d) Martínez, R.; Ram
2
1599e1605; (e) Martínez, R.; Zoli, L.; Cozzi, P. G.; Ram
oꢀ n, D. J.; Yus, M. Tetra-
2
hedron: Asymmetry 2008, 19, 2600e2607.
23. Martínez-Asencio, A.; Yus, M.; Ram
oꢀ n, D. J. Synthesis 2011, 3730e3740.
oꢀ n, D. J.; Yus, M. Angew. Chem., Int. Ed. 2007, 46,
7
8
24. (a) Guillena, G.; Ram
2358e2364; (b) Guillena, G.; Ram
1611e1641.
25. Cano, R.; Yus, M.; Ram
oꢀ n, D. J. Tetrahedron 2012, 68, 1393e1400.
26. Zhang, L.; Wang, S.; Zhou, S.; Yang, G.; Sheng, E. J. Org. Chem. 2006, 71,
3149e3153.
27. Van Baelen, G.; Maes, B. U. W. Tetrahedron 2008, 64, 5604e5619.
28. Li, Y.-T.; Liao, B.-S.; Chen, H.-P.; Liu, S.-T. Synthesis 2011, 2639e2643.
29. Cao, L.; Ding, J.; Gao, M.; Wang, Z.; Li, J.; Wu, A. Org. Lett. 2009, 11, 3810e3813.
30. Hiegel, G. A.; Hogenauer, T. J.; Lewis, J. C. Synth. Commun. 2005, 35, 2099e2105.
31. Liu, C.; He, C.; Shi, W.; Chen, M.; Lei, A. Org. Lett. 2007, 9, 5601e5604.
oꢀ n, D. J.; Yus, M. Chem. Rev. 2010, 110,
8
9
5
C.; Vavasori, A.; Bortoluzzi, M. J. Mol. Catal. A: Chem. 2008, 290, 79e87; (c)
Sharma, S. K.; Bishopp, S. D.; Allen, C. L.; Lawrence, R.; Bamford, M. J.; Lapkin, A.
A.; Plucinski, P.; Watson, R. J.; Williams, J. M. J. Tetrahedron Lett. 2011, 52,
4
252e4255; (d) Saidulu, G.; Anand, N.; Rao, K. S. R.; Burri, A.; Park, S.-E.; Burri,
D. R. Catal. Lett. 2011, 141, 1865e1871.
0. Owston, N. A.; Parker, A. J.; Williams, J. M. J. Org. Lett. 2007, 9, 3599e3601.
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