C-N bond-forming self-condensation of amide promoted by MoCl5 at room temperature

Inorganic Chemistry

Volumn 50, Issue 9, 2011, Pages 3846-3848

  Dolci, Sara ^a   Marchetti, Fabio ^a   Pampaloni, Guido ^a   Zacchini, Stefano ^b  

^a UNIVERSITY OF PISA   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79955443458     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic2001199     Document Type: Article

References (76)

1. Some recent references are as follows: Smitha, G.; Chandrasekhar, S.; Reddy, C. S. Synthesis 2008, 829 and references cited therein
2. Rodriguez-Cisterna, V.; Villar, C.; Romea, P.; Urpí, F. J. Org. Chem. 2007, 72, 6631
3. Mamat, C.; Büttner, S.; Trabhardt, T.; Fischer, C.; Langer, P. J. Org. Chem. 2007, 72, 6273
4. Basavaiah, D.; Reddy, K. R. Org. Lett. 2007, 9, 57
5. Nguyen, V. T. H.; Bellur, E.; Appel, B.; Langer, P. Synthesis 2006, 1103
6. Anastasia, L.; Giannini, E.; Zanoni, G.; Vidari, G. Tetrahedron Lett. 2005, 46, 5803
7. Kumar, S.; Manickam, M. Chem. Commun. 1997, 1615
8. Waldvogel, S. R. Synlett 2002, 622
9. Kramer, B.; Fröhlich, R.; Bergander, K.; Waldvogel, S. R. Synthesis 2003, 91
10. Coe, E. M.; Jones, C. J. Polyhedron 1992, 11, 3123
11. Reddy, C. R.; Mahipal, B.; Yaragorla, S. R. Tetrahedron Lett. 2007, 48, 7528
12. Guo, Q.; Miyaji, T.; Gao, G.; Hara, R.; Takahashi, T. Chem. Commun. 2001, 1018
13. Guo, Q.; Miyaji, T.; Hara, R.; Shen, B.; Takahashi, T. Tetrahedron 2002, 58, 7327
14. Guo, Q.; Li, L.; Chen, L.; Wang, Y.; Ren, S.; Shen, B. Energy Fuels 2009, 23, 51
15. Reddy, C. R.; Rao, N. N.; Sudhakar, A. Lett. Org. Chem. 2008, 5, 473
16. Hirao, T.; Kohno, S.; Enda, J.; Ohshiro, Y.; Agawa, T. Tetrahedron Lett. 1981, 22, 3633
17. Graham, J. R.; Slaugh, L. H. Tetrahedron Lett. 1971, 12, 787
18. Garner, C. D.; Charnock, J. M. In Comprehensive Coordination Chemistry; Wilkinson, G.; Gillard, R. D.; McCleverty, J. A., Eds.; Pergamon: Oxford, U.K., 1987; Vol. 3, pp 1329 - 1374.
19. Dori, Z. In Comprehensive Coordination Chemistry; Wilkinson, G.; Gillard, R. D.; McCleverty, J. A., Eds.; Pergamon: Oxford, U.K., 1987; Vol. 3, pp 973 - 1022.
20. Young, C. G. In Comprehensive Coordination Chemistry II; McCleverty, J. A.; Meyer, T. J., Eds.; Elsevier: Oxford, U.K., 2003; Vol. 4, pp 415 - 527.
21. Okamura, T.; Ueyama, N. In Comprehensive Coordination Chemistry II; McCleverty, J. A.; Meyer, T. J., Eds.; Elsevier: Oxford, U.K., 2003; Vol. 4, pp 529 - 573.
22. Larson, M. L. J. Am. Chem. Soc. 1960, 82, 1223
23. Kepert, D. L.; Mandyczewsky, R. J. Chem. Soc. A 1968, 530
24. Ernst, T.; El-Kholi, A.; Müller, U.; Dehnicke, K. Z. Anorg. Allg. Chem. 1988, 566, 7
25. Hyde, J.; Magin, L.; Zubieta, J. J. Chem. Soc., Chem. Commun. 1980, 204
26. Horner, S. M.; Tyree, S. Y., Jr. Inorg. Chem. 1962, 1, 122
27. Dolci, S.; Marchetti, F.; Pampaloni, G.; Zacchini, S. Dalton Trans. 2010, 39, 5367
28. Düz, B.; Elbistan, C. K.; Ece, A.; Sevin, F. Appl. Organomet. Chem. 2009, 23, 359
29. Masuda, T.; Hasegawa, K.; Higashimura, T. Macromolecules 1974, 7, 728
30. Masuda, T.; Okano, Y.; Kuwane, Y.; Higashimura, T. Polym. J. 1980, 12, 907
31. Naylor, F. E. U.S. Patent 3,336,280, 1967.
32. Zhang, L.; Zhou, D.; Ye, Y.; Liu, G.; Feng, E.; Jiang, H.; Liu, H. J. Org. Chem. 2010, 75, 3671
33. Bian, Y.-J.; Liu, X.-Y.; Ji, K.-G.; Shu, X.-Z.; Guo, L.-N.; Liang, Y.-M. Tetrahedron 2009, 65, 1424
34. Bolshan, Y.; Batey, R. A. Angew. Chem., Int. Ed. 2008, 47, 2109
35. Fernandes, A. C.; Româo, C. C. J. Mol. Catal. A: Chem. 2007, 272, 60
36. Nath, D. C. D.; Fellows, C. M.; Kobayashi, T.; Hayashi, T. Aust. J. Chem. 2006, 59, 218
37. Patil, N. T.; Huo, Z.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2006, 71, 3612
38. Martin, R.; Rodriguez Rivero, M.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 7079
39. Goossen, L. J.; Rauhaus, J. E.; Deng, G. Angew. Chem., Int. Ed. 2005, 44, 4042
40. Schwartz, D.; Heyer, R. J. Inorg. Nucl. Chem. 1967, 29, 1384
41. Gerrard, W.; Lappert, M. F.; Wallis, J. W. J. Chem. Soc. 1960, 2141
42. Marchetti, F.; Pampaloni, G.; Zacchini, S. Eur. J. Inorg. Chem. 2008, 453 and references cited therein
43. See the Supporting Information.
44. Fenske, D.; Jansen, K.; Dehnicke, K. Z. Naturforsch. 1986, 41B, 523
45. Allenstein, E.; Keller, K.; Hausen, H.-D.; Weidlein, J. Z. Anorg. Allg. Chem. 1987, 554, 188
46. Hvoslef, J.; Tracy, M. L.; Nash, C. P. Acta Crystallogr., Sect. C 1986, 42, 353
47. -1 in uncoordinated MeC(O)NHPh.
48. Piovesana, O.; Furlani, C. Inorg. Nucl. Chem. Lett. 1967, 3, 535
49. Lever, A. B. P. Inorganic Electronic Spectroscopy, 2nd ed.; Elsevier: Amsterdam, The Netherlands, 1984.
50. Collison, D. J. Chem. Soc., Dalton Trans. 1990, 2999
51. Bosshard, H. H.; Zollinger, Hch. Helv. Chim. Acta 1959, 42, 1659
52. Kantlehner, W. In Advances in Organic Chemistry; Böhme, H.; Viehe, H. G., Eds.; Wiley: New York, 1979; pp 6 - 58 and references cited therein.
53. Helbert, M.; Renou, J. P.; Martin, M. L. Tetrahedron 1979, 35, 1087
54. Martin, M. L.; Ricolleau, G.; Poignant, S.; Martin, G. J. J. Chem. Soc., Perkin Trans. 2 1976, 182
55. Jutz, C. In Advances in Organic Chemistry; Böhme, H.; Viehe, H. G., Eds.; Wiley: New York, 1976; pp 226 - 341 and references cited therein.
56. Hamed, A.; Müller, E.; Jochims, J. C. Tetrahedron 1986, 42, 6645
57. - salts have been reported. Beck, J.; Koch, M. Z. Anorg. Allg. Chem. 2006, 632, 756
58. Baumann, A.; Beck, J. Z. Anorg. Allg. Chem. 1998, 624, 1725
59. Beck, J.; Hengstmann, M. Z. Naturforsch. 1996, 51B, 1415
60. Lindsay, K. B.; Ferrando, F.; Christensen, K. L.; Overgaard, J.; Roca, T.; Bennasar, M.-L.; Skrydstrup, T. J. Org. Chem. 2007, 72, 4181
61. Rangareddy, K.; Selvakumar, K.; Harrod, J. F. J. Org. Chem. 2004, 69, 6843
62. Selvakumar, K.; Harrod, J. F. Angew. Chem., Int. Ed. 2001, 40, 2129
63. Kashimura, S.; Ishifune, M.; Murai, Y.; Murase, H.; Shimomura, M.; Shono, T. Tetrahedron Lett. 1998, 39, 6199
64. Ogawa, A.; Nanke, T.; Takami, N.; Sekiguchi M.; Kambe, N.; Sonoda, N. Appl. Organomet. Chem. 1995, 9, 461
65. Jochims, J. C.; Abu-El-Halawa, R. Synthesis 1990, 488 and references cited therein
66. Brosshard, H. H.; Mory, R.; Schmid, M.; Zollinger, Hch. Helv. Chim. Acta 1959, 42, 1653
67. Li, P.; Xu, J.-C. Tetrahedron 2000, 56, 4437
68. Meth-Cohn, O.; Stanforth, S. P. The Vilsmeier-Haack Reaction. In Comprehensive Organic Synthesis; Trost, B. M; Fleming, I., Eds.; Elsevier: Amsterdam, The Netherlands, 1991; Vol. 3, pp 777 - 794.
69. Hamed, A.; Müller, E.; Al-Talib, M.; Jochims, J. C. Synthesis 1987, 745
70. Williams, J. M.; Peterson, S. W.; Brown, G. M. Inorg. Chem. 1968, 7, 2577
71. Matkovic, B.; Peterson, S. W.; Williams, J. M. Croat. Chem. Acta 1967, 39, 139
72. Chem. Abstr. 1968, 68, 82133.
73. Bulychev, B.; Bel'skii, V. K. Russ. J. Inorg. Chem. 1995, 40, 1834
74. Hitzler, M. G.; Freyhardt, C. C.; Jochims, J. C. Synthesis 1994, 509
75. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1
76. Kaufmann, G.; Leroy, M. F. J. Bull. Soc. Chim. Fr. 1967, 402