Iron-catalyzed redox radical cyclizations of 1,6-dienes and enynes

Organic Letters

Volumn 12, Issue 1, 2010, Pages 112-115

  Taniguchi, Tsuyoshi ^a   Goto, Naoya ^a   Nishibata, Asami ^a   Ishibashi, Hiroyuki ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FERRIC CHLORIDE; FERRIC ION; HETEROCYCLIC COMPOUND; IRON; POLYENE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; SYNTHESIS;

CATALYSIS; CYCLIZATION; FERRIC COMPOUNDS; HETEROCYCLIC COMPOUNDS; IRON; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; POLYENES;

EID: 73949140641     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902562j     Document Type: Article

References (65)

1. For reviews, see: (a) Renaud, P.; Sibi, M. P. Radical in Organic Synthesis; Wiley-VCH: Weinheim, 2001.
2. (b) Gansäuer, A., Ed.; Topics Current Chemistry; Radicals in Synthesis I and II; Springer: Berlin; 2006; Vols. 263 and 264.
3. For selected recent examples, see: (a) Schaffner, A.-P.; Darmency, V.; Renaud, P. Angew. Chem., Int. Ed. 2006, 45, 5847.
4. (b) Medeiros, M. R.; Schacherer, L. N.; Spiegel, D. A.; Wood, J. L. Org. Lett. 2007, 9, 4427.
5. (c) Smith, D. M.; Pulling, M. E.; Norton, J. R. J. Am. Chem. Soc. 2007, 129, 770.
6. (d) Gansäuer, A.; Fan, C.-A.; Piestert, F. J. Am. Chem. Soc. 2008, 130, 6916.
7. (e) Ueng, S.-H.; Makhlouf Brahmi, M.; Derat, E.; Fensterbank, L.; Lacôte, E.; Malacria, M.; Curran, D. P. J. Am. Chem. Soc. 2008, 130, 10082.
8. (f) Quiclet-Sire, B.; Zard, S. Z. Org. Lett. 2008, 10, 3279.
9. (g) Akindele, T.; Yamada, K.; Tomioka, K. Acc. Chem. Res. 2009, 42, 345.
10. (h) Friestad, G. K.; Banerjee, K. Org. Lett. 2009, 11, 1095.
11. For reviews, see: (a) Iron Catalysis in Organic Chemistry; Plietker, B., Ed.; Wiley-VCH: Weinheim, 2008.
12. (b) Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217.
13. (c) Fürstner, A.; Martin, R. Chem. Lett. 2005, 34, 624.
14. (d) Correa, A.; Mancheño, O. G.; Bolm, C. Chem. Soc. Rev. 2008, 37, 1108.
15. (e) Enthaler, S.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2008, 47, 3317.
16. (f) Sherry, B. D.; Fürstner, A. Acc. Chem. Res. 2008, 47, 1500.
17. (g) Correa, A.; García Mancheño, O.; Bolm, C. Chem. Soc. Rev. 2008, 37, 1108.
18. (h) Fürstner, A. Angew. Chem., Int. Ed. 2009, 48, 1364.
19. Okamoto, T.; Oka, S. J. Org. Chem. 1984, 49, 1589.
20. 2 and silanes have been reported by Mukaiyama and co-workers; see: (a) Mukaiyama, T.; Isayama, S.; Inoki, S.; Kato, K.; Yamada, T.; Takai, T. Chem. Lett. 1989, 449.
21. (b) Inoki, S.; Kato, K.; Takai, T.; Isayama, S.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1989, 515.
22. (c) Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 1071.
23. (d) Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 569.
24. (e) Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 573.
25. (f) Kato, K.; Yamada, T.; Takai, T.; Inoki, S.; Isayama, S. Bull. Chem. Soc. Jpn. 1990, 63, 179.
26. (g) Isayama, S. Bull. Chem. Soc. Jpn. 1990, 63, 1305.
27. Recently, Carreira and co-workers have reported the cobalt-catalyzed functionalization of inactive alkenes; see: (a) Waser, J.; Nambu, H.; Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 8294.
28. (b) Waser, J.; González-Gómez, J. C.; Nambu, H.; Huber, P.; Carreira, E. M. Org. Lett. 2005, 7, 4249.
29. (c) Waser, J.; Gaspar, B.; Nambu, H.; Carreira, E. M. J. Am. Chem. Soc. 2006, 128, 11693.
30. (d) Gaspar, B.; Carreira, E. M. Angew. Chem., Int. Ed. 2007, 46, 4519.
31. (e) Gaspar, B.; Waser, J.; Carreira, E. M. Synthesis 2007, 3839.
32. (f) Gaspar, B.; Carreira, E. M. Angew. Chem., Int. Ed. 2008, 47, 5758.
33. Prateeptongkum, S.; Jovel, I.; Jackstell, R.; Vogl, N.; Weckbecker, C.; Beller, M. Chem. Commun. 2009, 1990.
34. Ishikawa, H.; Colby, D. A.; Seto, S.; Va, P.; Tam, A.; Kakei, H.; Rayl, T. J.; Hwang, I.; Boger, D. L. J. Am. Chem. Soc. 2009, 131, 4904.
35. For examples of iron-mediated radical cyclizations, see: (a) Cabri, W.; Borghi, D.; Arlandini, E.; Sbraletta, P.; Bedeschi, A. Tetrahedron 1993, 49, 6837.
36. (b) Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315.
37. (c) Booker-Milburn, K. I.; Barker, A.; Brailsford, W.; Cox, B.; Mansley, T. E. Tetrahedron 1998, 54, 15321.
38. (d) Jahn, P.; Hartmann, P. Chem. Commun. 1998, 209.
39. (e) Bach, T.; Schlummer, B.; Harms, K. Chem. Commun. 2000, 287.
40. (f) Booker-Milburn, K. I.; Jones, J. L.; Sibley, G. E. M.; Cox, R.; Meadows, J. Org. Lett. 2003, 5, 1107.
41. For selected recent examples of radical cyclizations of 1,6-dienes, see: (a) Ueda, M.; Miyabe, H.; Nishimura, A.; Miyata, O.; Takemoto, Y.; Naito, T. Org. Lett. 2003, 5, 3835.
42. (b) Schmidt, B.; Pohler, M.; Costisella, B. J. Org. Chem. 2004, 69, 1421.
43. (c) James, P.; Schenk, K.; Landais, Y. J. Org. Chem. 2006, 71, 3630.
44. (d) Hirai, T.; Han, L.-B. Org. Lett. 2007, 9, 53.
45. (e) Mantrand, N.; Renaud, P. Tetrahedron 2008, 64, 11860.
46. (f) Sánchez, E. M.; Arteaga, J. F.; Domingo, V.; Quílez del Moral, J. F.; Mar Herrador, M.; Barrero, A. F. Tetrahedron 2008, 64, 5111.
47. cis-Isomers for 2a and 3a were assumed to be major products, since radical cyclizations of 1,6-dienes generally afforded cis products; see: Tripp, J. C.; Schiesser, C. H.; Curran, D. P. J. Am. Chem. Soc. 2006, 127, 5518.
48. In the reaction of 1a, simple hydrochlorinated or hydrated product of olefin was also detected by NMR analysis of the crude product.
49. 2]; see: (a) Schaeffer, G. W.; Roscoe, J. S.; Stewart, A. C. J. Am. Chem. Soc. 1956, 78, 729.
50. (b) Glavee, G. N.; Klabunde, K. J.; Sorensen, C. M.; Hadjipanayis, G. C. Inorg. Chem. 1995, 34, 28.
51. 3SiH was used as a hydride source, no reaction occurred.
52. For a recent review of catalytic enyne cyclizations, see: Michelet, V.; Toullec, P. Y.; Genêt, J.-P. Angew. Chem., Int. Ed. 2008, 47, 4268.
53. Indium-madiated reductive radical cyclizations of enynes have been reported; see: (a) Takami, K.; Mikami, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2003, 68, 6627.
54. (b) Miura, K.; Fujisawa, N.; Hosomi, A. J. Org. Chem. 2004, 69, 2427.
55. (c) Hayashi, N.; Shibata, I.; Baba, A. Org. Lett. 2004, 6, 4981.
56. (d) Hayashi, N.; Shibata, I.; Baba, A. Org. Lett. 2005, 7, 3093.
57. Quite recently, the iron-catalyzed reductive cyclization of 1,6-enynes and diynes has been reported; see: (a) Sylvester, K. T.; Chirik, P. J. J. Am. Chem. Soc. 2009, 131, 8772.
58. For recent examples of the synthesis of vinyl halides using iron catalyst, see: (a) Miranda, P. O.; Diaz, D. D.; Padrón, J. I.; Bermejo, J.; Martín, V. S. Org. Lett. 2003, 11, 1979.
59. (b) Miranda, P. O.; Díaz, D. D.; Padrón, J. I.; Ramírez, M. A.; Martín, V. S. J. Org. Chem. 2005, 70, 57.
60. (c) Carballo, R. M.; Ramírez, M. A.; Rodríguez, M. L.; Martín, V. S.; Padrón, J. I. Org. Lett. 2006, 8, 3837.
61. (d) Miranda, P. O.; Carballo, R. M.; Martin, V. S.; Padrón, J. I. Org. Lett. 2009, 11, 357.
62. (e) Xu, T.; Yu, Z.; Wang, L. Org. Lett. 2009, 11, 2113.
63. (f) Cantagrel, G.; Carné-Carnavalet, B.; Meyer, C.; Cossy, J. Org. Lett. 2009, 11, 4262.
64. The reaction of enyne substrates using method B gave a complex mixture of products.
65. Sugimori, T.; Horike, S.-i.; Tsumura, S.; Honda, M.; Kasuga, K. Inorg. Chim. Acta 1998, 283, 275.