Copper-catalyzed vinylation of hydrazides. A regioselective entry to highly substituted pyrroles

Organic Letters

Volumn 9, Issue 6, 2007, Pages 973-976

  Rodríguez Rivero, Marta ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; HYDRAZINE DERIVATIVE; PYRROLE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; COPPER; CYCLIZATION; HYDRAZINES; MODELS, CHEMICAL; PYRROLES; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 33947599298     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062978s     Document Type: Article

References (47)

1. (a) Agarwal, S.; Cämmerer, S.; Filali, S.; Frohner, W.; Knöll, J.; Krahl, M. P.; Reddy, K. R.; Knölker, H.-J. Curr. Org. Chem. 2005, 9, 1601.
2. (b) Fürstner, A. Angew. Chem. Int. Ed. 2003, 42, 3528.
3. (c) Hoffmann, H.; Lindel, T. Synthesis 2003, 1753.
4. (d) O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435.
5. (e) Joule, J. A.; Mills, K. Heterocyclic Chemistry; Blackwell Science: Oxford, 2000.
6. (a) Custelcean, R.; Delmau, L. H.; Moyer, B. A.; Sessler, J. L.; Cho, W.-S.; Gross, D.; Bates, G. W.; Brooks, S. J.; Light, M. E.; Gale, P. A. Angew. Chem., Int. Ed. 2005, 44, 2537.
7. (b) Domingo, V. M.; Aleman, C.; Brillas, E.; Julia, L. J. Org. Chem. 2001, 66, 4058.
8. (a) Knorr, L. Ber. 1884, 17, 1635.
9. For recent examples: (b) Shiner, C. M.; Lash, T. D. Tetrahedron 2005, 61, 11628.
10. (c) Bellingham, R. K.; Carey, J. S.; Hussain, N.; Morgan, D. O.; Oxley, P.; Powling, L. C. Org. Process Res. Dev. 2004, 8, 279.
11. (d) Manley, J. M.; Kalman, M. J.; Conway, B. G.; Ball, C. C.; Havens, J. L.; Vaidyanathan, R. J. Org. Chem. 2003, 68, 6447.
12. (a) Hantzsch, A. Ber. 1890, 23, 1474.
13. For recent examples: (b) Matiychuk, V. S.; Martyak, R. L.; Obushak, N. D.; Ostapiuk, Y. V.; Pidlypnyi, N. I. Chem. Heterocycl. Comp. 2004, 40, 1218.
14. (c) Calvo, L.; González-Ortega, A.; Sañudo, M. C. Synthesis 2002, 2450.
15. (d) Trautwein, A. W.; Süßmuth, R. D.; Jung, G. Bioorg. Med. Chem. Lett. 1998, 8, 2381.
16. (a) Paal, C. Ber. 1885, 18, 367.
17. (b) Knorr, L. Ber. 1885, 18, 299.
18. For recent examples: (c) Chen, J.; Wu, H.; Zheng, Z.; Jin, C.; Zhang, X.; Su, W. Tetrahedron Lett. 2006, 47, 5383.
19. (d) Minetto, G.; Raveglia, L. F.; Sega, A.; Taddei, M. Eur. J. Org. Chem. 2005, 5277.
20. (e) Banik, B. K.; Banik, I.; Renteria, M.; Dasgupta, S. K. Tetrahedron Lett. 2005, 46, 2643.
21. For some reviews on synthesis of pyrroles: (a) Balme, G. Angew. Chem. Int. Ed. 2004, 43, 6238.
22. (b) Ferreira, V. F.; de Souza, M. C. B. V.; Cunha, A. C.; Pereira, L. O. R.; Ferreira, M. L. G. Org. Prep. Proced. Int. 2001, 33, 411.
23. For recent syntheses of pyrroles: (a) Hiroya, K.; Matsumoto, S.; Ashikawa, M.; Ogiwara, K.; Sakamoto, T. Org. Lett. 2006, 8, 5349.
24. (b) Fuchibe, K.; Ono, D.; Akiyama, T. Chem. Commun. 2006, 2271.
25. (c) Dong C.; Deng, G.; Wang, J. J. Org. Chem. 2006, 71, 5560.
26. (d) Binder, J. T.; Kirsch, S. F. Org. Lett. 2006, 8, 2151.
27. (e) Lu, L.; Chen, G.; Ma, S. Org. Lett. 2006, 8, 835.
28. (f) Harrison, T. J.; Kozak, J. A.; Corbella-Pané, M.; Dake, G. R. J. Org. Chem. 2006, 71, 4525.
29. (g) Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260.
30. (a) Piloty, O. Ber. 1910, 43, 489.
31. (b) Robinson, G. M.; Robinson, R. J. Chem. Soc. 1918, 43, 639.
32. (a) Posvic, H.; Dombro, R.; Ito, H.; Telinski, T. J. Org. Chem. 1974, 39, 2575.
33. (b) Baldwin, J. E.; Bottaro, J. C. J. Chem. Soc., Chem. Commun. 1982, 624.
34. Martín, R.; Rodríguez Rivero, M.; Buchwald, S. L. Angew. Chem. Int. Ed. 2006, 45, 7079.
35. For recent reviews on palladium-catalyzed C-N bond-forming reactions: (a) Hartwig, J. F. Synlett 2006, 1283.
36. (b) Jiang, L.; Buchwald, S. L. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; p 699.
37. For recent reviews on Cu-catalyzed C-N bond-forming reactions: (a) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
38. (b) Ley, S. V.; Thomas, A. W. Angew. Chem. Int. Ed. 2003, 42, 5400.
39. (c) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428.
40. Two examples for the metal-catalyzed syntheses of monosubstituted vinyl hydrazides from alkenyl boronic acids have been previously reported in the literature: (a) Uemura, T.; Chatani, N. J. Org. Chem. 2005, 70, 8631.
41. (b) Kabalka, G. W.; Guchhait, S. K. Org. Lett. 2003, 5, 4129.
42. During the revision process of this manuscript, the Pd-catalyzed coupling between tert-butyl carbazate and vinyl halides was reported: (c) Barluenga, J.; Moriel, P.; Aznar, F.; Valdés, C. Org. Lett. 2007, 9, 275.
43. NOESY experiments for compounds in entries 3 and 5 (Table 1) indicate that the double bond geometry of the starting vinyl iodides is retained in the product.
44. The use of several Lewis acids to catalyze the [3,3] rearrangement was tested. However, only decomposition products were obtained.
45. For the isolation of similar intermediates in the Fischer indole synthesis: (a) Tullberg, E.; Schacher, F.; Peters, D.; Frejd, T. Synthesis 2006, 1183.
46. (b) Miyata, O.; Kimura, Y.; Naito, T. Synthesis 2001, 1635.
47. Starting vinyl iodides were readily prepared, generally in one or two steps, from commercially available materials. For details, see the Supporting Information.