With molecular-oxygen-activated Lewis acids: Dinuclear molybdenum complexes for aza-Diels-Alder reactions of acyl hydrazones

Angewandte Chemie - International Edition

Volumn 45, Issue 23, 2006, Pages 3816-3819

  Yamashita, Yasuhiro ^a   Salter, Matthew M ^a   Aoyama, Kayoko ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Aza Diels Alder reaction; Homogeneous catalysis; Lewis acids; Molybdenum; Oxygen activation

Indexed keywords

ACTIVATION ANALYSIS; ALCOHOLS; ALDEHYDES; CATALYSIS; COMPLEXATION; NITROGEN COMPOUNDS; ORGANIC ACIDS; OXYGEN; REACTION KINETICS;

AZA DIELS ALDER REACTION; HOMOGENEOUS CATALYSIS; LEWIS ACIDS; OXYGEN ACTIVATION;

MOLYBDENUM COMPOUNDS;

HYDRAZONE DERIVATIVE; MOLYBDENUM; OXYGEN; PIPERIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY;

CATALYSIS; HYDRAZONES; MOLYBDENUM; OXYGEN; PIPERIDINES;

EID: 33746238134     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200600801     Document Type: Article

References (29)

1. Lewis Acids in Organic Synthesis (Ed.: H. Yamamoto), Wiley-VCH, Weinheim, 2000.
2. a) C. D. Garner in Comprehensive Coordination Chemistry, Vol. 3 (Eds.: G. Wilkinson, R. D. Gillard, J. A. McCleverty), Pergamon, Oxford, 1987, chap. 36.3, p. 1301;
3. b) F. H. Jardine, P. S. Sheridan in Comprehensive Coordination Chemistry, Vol. 4 (Eds.: G. Wilkinson, R. D. Gillard, J. A. McCleverty), Pergamon, Oxford, 1987, chap. 48, p. 901;
4. J. L. Eglin in Comprehensive Coordination Chemistry II, Vol. 4 (Eds.: J. A. McCleverty, T. J. Meyer), Pergamon, Oxford, 2004, chap. 4.9, p. 575.
5. For organic reactions using molybdenum dimer complexes, see: a) M. McCann in Catalysis by Di- and Polynuclear Metal Cluster Complexes (Eds.: A. D. Adams, F. A. Cotton), Wiley-VCH, New York, 1998, chap. 5, p. 145;
6. for asymmetric hetero Diels-Alder reactions using chiral Rh dimer complexes, see b) M. P. Doyle, I. M. Phillips, W. Hu, J. Am. Chem. Soc. 2001, 125, 5366;
7. M. Valenzuela, M. P. Doyle, C. Hedberg, W. Hu, A. Holmstrom, Synlett 2004, 2425;
8. M. P. Doyle, M. Valenzuela, P. Huang, Proc. Natl. Acad. Sci. USA 2004, 101, 5391;
9. e) R. E. Forslund, J. Cain, J. Colyer, M. P. Doyle, Adv. Synth. Catal. 2005, 347, 87;
10. f) M. Anada, T. Washio, N. Shimada, S. Kitagaki, M. Nakajima, M. Shiro, S. Hashimoto, Angew. Chem. 2004, 116, 2719;
11. Angew. Chem. Int. Ed. 2004, 43, 2665;
12. 4] as a stoichiometric Lewis acid, see: g) H. Hirao, Y. Fujihara, S. Tsuno, Y. Ohshiro, T. Agawa, Chem. Lett. 1984, 367.
13. Y. Yamashita, Y. Mizuki, S. Kobayashi, Tetrahedron Lett. 2005, 46, 1803.
14. M. J. Burk, J. E. Feaster, J. Am. Chem. Soc. 1992, 114, 6266, and also see Ref. [6].
15. a) H. Oyamada, S. Kobayashi, Synlett 1998, 249;
16. b) S. Kobayashi, T. Furuta, K. Sugita, H. Oyamada, Synlett 1998, 1019;
17. S. Kobayashi, Y. Hasegawa, H. Ishitani, H. Chem. Lett. 1998, 1131;
18. S. Kobayashi, K. Sugita, H. Oyamada, Synlett 1999, 138;
19. e) K. Manabe, H. Oyamada, K. Sugita, S. Kobayashi, J. Org. Chem. 1999, 64, 8054;
20. f) O. Okitsu, H. Oyamada, T. Furuta, S. Kobayashi, Heterocycles 2000, 52, 1143;
21. g) M. Sugiura, S. Kobayashi, Angew. Chem. Int. Ed. 2005, 44, 5176.
22. An alternative radical pathway that accounts for C-C bond-forming reactions in the presence of metal catalysts and molecular oxygen can be proposed. We investigated the effect of adding a radical scavenger (2,4,6-tri-tert-butylphenol, 20 mol%) to the reaction; almost no effect was observed and the product heterocycle was obtained in 71 % yield under the conditions shown in Table 1, entry 14.
23. A. B. Brignole, F. A. Cotton, Inorg. Synth. 1972, 13, 81.
24. The use of monomeric Mo species as Lewis acids has been documented: a) H. Dvořákova, D. Dvořák, J. Šrogi, P. Kocovsky, Tetrahedron Lett. 1995, 36, 6351;
25. b) A. V. Malkov, I. Baxendale, D. J. Mansfield, P. Kocovsky. Tetrahedron Lett. 1997, 4895;
26. A. V. Malkov, I. R. Baxendale, D. Dvořák, D. J. Mansfield, P. Kocovsky, J. Org. Chem. 1999, 64, 2737;
27. A. V. Malkov, S. L. Davis, W. L. Mitchell, P. Kocovsky, J. Org. Chem. 1999, 64, 2751;
28. e) A. Sakakura, R. Kondon, K. Ishihara, Org. Lett. 2005, 7, 1974, and references therein.
29. F. A. Cotton, L. M. Daniels, C. A. Murillo, J. G. Slaton J. Am. Chem. Soc. 2002, 124, 2878.