(1-Alkynyl)dicarbonylcyclopentadienyliron complexes as electron-rich alkynes in organic synthesis: BF3-mediated [2+2] cycloaddition/ring- opening providing (2-alkenyl-1-imino)iron complexes

Chemistry - A European Journal

Volumn 17, Issue 31, 2011, Pages 8559-8561

  Nakaya, Ryotaro ^a   Yasuda, Shigeo ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

amides; cleavage reactions; cycloaddition; iron; schiff bases

Indexed keywords

AROMATIC ALDEHYDE; CLEAVAGE REACTION; ELECTRON-RICH; IRON COMPLEX; ORGANIC SYNTHESIS; OXIDATIVE CONDITIONS; RING OPENING; SCHIFF BASIS;

ACETYLENE; ALDEHYDES; AMIDES; FUNCTIONAL GROUPS; IRON; SUBSTITUTION REACTIONS;

IRON COMPOUNDS;

ALKENE; ALKYNE; BORANE DERIVATIVE; BORON TRIFLUORIDE ETHERATE; IRON DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALKENES; ALKYNES; BORANES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; IRON COMPOUNDS; MOLECULAR STRUCTURE;

EID: 79960543871     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201100669     Document Type: Article

References (56)

1. Reviews: (a)B. Alcaide, P. Almendros, C. Aragoncillo, Chem. Soc. Rev. 2010, 39, 783-816
2. W. Tam, J. Goodreid, N. Cockburn, Curr. Org. Synth. 2009, 6, 219-238
3. T. Kondo, Synlett 2008, 629-644
4. V. López-Carrillo, A. M. Echavarren, J. Am. Chem. Soc. 2010, 132, 9292-9294 and references cited therein.
5. M. L. M. Pennings, D. N. Reinhoudt, J. Org. Chem. 1982, 47, 1816-1823
6. J. J. Eisch, J. E. Galle, L. E. Hallenbeck, J. Org. Chem. 1982, 47, 1608-1610
7. W. Verboom, P. J. S. S. van Eijk, P. G. M. Conti, D. N. Reinhoudt, Tetrahedron 1989, 45, 3131-3138
8. A. L. Kohnen, X. Y. Mak, T. Y. Lam, J. R. Dunetz, R. L. Danheiser, Tetrahedron 2006, 62, 3815-3822
9. H. Li, R. P. Hsung, K. A. DeKorver, Y. Wei, Org. Lett. 2010, 12, 3780-3783
10. S. Kato, F. Diederich, Chem. Commun. 2010, 46, 1994-2006
11. L. You, Z. F. Al-Rashid, R. Figueroa, S. K. Ghosh, G. Li, T. Lu, R. P. Hsung, Synlett 2007, 1656-1662
12. K. C. M. Kurtz, R. P. Hsung, Y. Zhang, Org. Lett. 2006, 8, 231-234.
13. C. J. Kowalski, G. S. Lal, J. Am. Chem. Soc. 1988, 110, 3693-3695
14. M. Shindo, Tetrahedron Lett. 1997, 38, 4433-4436
15. R. F. Sweis, M. P. Schramm, S. A. Kozmin, J. Am. Chem. Soc. 2004, 126, 7442-7443.
16. K. Narasaka, Y. Hayashi, H. Shimadzu, S. Niihata, J. Am. Chem. Soc. 1992, 114, 8869-8885
17. H. Ito, M. Hasegawa, Y. Takenaka, T. Kobayashi, K. Iguchi, J. Am. Chem. Soc. 2004, 126, 4520-4521.
18. M. Koketsu, M. Kanoh, H. Ishihara, Synlett 2002, 805-806
19. M. Koketsu, K. Mizutani, T. Ogawa, A. Takahashi, H. Ishihara, J. Org. Chem. 2004, 69, 8938-8941.
20. Reviews:(a) A. J. Pearson, Iron Compounds in Organic Synthesis, Academic Press, London, 1994
21. A. J. Pearson, Pure Appl. Chem. 1983, 55, 1767-1779
22. H.-J. Knölker, Curr. Org. Synth. 2004, 1, 309-331
23. H.-J. Knölker, Chem. Rev. 2000, 100, 2941-2961
24. H.-J. Knölker, Chem. Soc. Rev. 1999, 28, 151-157
25. K. Rück-Braun, M. Mikulás, P. Amrhein, Synthesis 1999, 727-744
26. C.-J. Li, R.-S. Liu, Chem. Rev. 2000, 100, 3127-3161
27. A. S. Abd-El-Aziz, S. Bernardin, Coord. Chem. Rev. 2000, 203, 219-267
28. W. A. Donaldson, Curr. Org. Chem. 2000, 4, 837-868
29. H. Nakazawa, M. Itazaki, K. Kamata, K. Ueda, Chem. Asian J. 2007, 2, 882-888
30. C. E. Anson, A. V. Malkov, C. Roe, E. J. Sandoe, G. R. Stephenson, Eur. J. Org. Chem. 2008, 196-213 and references cited therein.
31. S. Yasuda, H. Yorimitsu, K. Oshima, Organometallics 2008, 27, 4025-4027
32. Y. Asada, S. Yasuda, H. Yorimitsu, K. Oshima, Organometallics 2008, 27, 6050-6052
33. S. Yasuda, Y. Asada, H. Yorimitsu, K. Oshima, Materials 2009, 2, 978-991
34. S. Yasuda, H. Yorimitsu, K. Oshima, Organometallics 2009, 28, 4872-4875
35. S. Yasuda, H. Yorimitsu, K. Oshima, Organometallics 2010, 29, 273-274
36. S. Yasuda, H. Yorimitsu, K. Oshima, Organometallics 2010, 29, 2634-2636.
37. R. Nakaya, S. Yasuda, H. Yorimitsu, K. Oshima, Tetrahedron Lett. 2009, 50, 5274-5276.
38. A. Davison, J. P. Solar, J. Organomet. Chem. 1979, 166, C 13 -C 17
39. M. I. Bruce, D. N. Duffy, M. J. Liddell, M. R. Snow, E. R. T. Tiekink, J. Organomet. Chem. 1987, 335, 365-378
40. M. I. Bruce, M. J. Liddell, M. R. Snow, E. R. T. Tiekink, Organometallics 1988, 7, 343-350
41. A. G. M. Barrett, N. E. Carpenter, J. Mortier, M. Sabat, Organometallics 1990, 9, 151-156
42. H. Fischer, F. Leroux, G. Roth, R. Stumpf, Organometallics 1996, 15, 3723-3731.
43. D. J. Armitt, M. I. Bruce, J. C. Morris, B. W. Skelton, A. H. White, J. Organomet. Chem. 2009, 694, 1-4 and references cited therein.
44. M. I. Bruce, T. W. Hambley, M. R. Snow, A. G. Swincer, Organometallics 1985, 4, 494-500.
45. C. Kelley, N. Lugan, M. R. Terry, G. L. Geoffroy, B. S. Haggerty, A. L. Rheingold, J. Am. Chem. Soc. 1992, 114, 6735-6749.
46. M. Hussain, D. Albert, R. Wartchow, H. Butenschön, Chem. Asian J. 2007, 2, 782-793.
47. Reactions of 1-alkynyliron complexes with tetracyanoethylene are sometimes known to result in similar tandem [2+2] cycloaddition/ring-opening. See refs [9 b] and [9 c].
48. For examples of tandem [2+2] cycloaddition/ring-opening in organic synthesis, see: (a)M. Shindo, S. Oya, R. Murakami, Y. Sato, K. Shishido, Tetrahedron Lett. 2000, 41, 5947-5950
49. P. Kraft, C. Denis, W. Eichenberger, Eur. J. Org. Chem. 2001, 2363-2369
50. P. O. Miranda, D. D. Díaz, J. I. Padrón, M. A. Ramírez, V. S. Martín, J. Org. Chem. 2005, 70, 57-62
51. T. Ishihara, T. Mantani, T. Konno, H. Yamanaka, Tetrahedron 2006, 62, 3783-3793
52. J. Y. Park, P. R. Ullapu, H. Choo, J. K. Lee, S.-J. Min, A. N. Pae, Y. Kim, D.-J. Baek, Y. S. Cho, Eur. J. Org. Chem. 2008, 5461-5469. Also see ref. [2 f] and [2 h].
53. C. Amiens, G. Balavoine, F. Guibé, J. Organomet. Chem. 1993, 443, 207-219.
54. H.-J. Cristau, A. Perraud-Darcy, Y. Ribeill, Tetrahedron Lett. 1992, 33, 2693-2696
55. H. Hoberg, B. W. Oster, J. Organomet. Chem. 1982, 234, C 35 -C 38
56. J. H. Park, S. Y. Kim, S. M. Kim, Y. K. Chung, Org. Lett. 2007, 9, 2465-2468.