An alkyne metathesis-based route to ortho-dehydrobenzannulenes

Synlett

Volumn , Issue 1, 2003, Pages 29-34

  Miljanić, Ognjen Š ^a   Vollhardt, K Peter C ^a   Whitener, Glenn D ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

1,2 di(prop 1 ynyl)arenes; Alkyne metathesis; Dehydrobenzannulenes; Microwave irradiation; Sonogashira coupling

Indexed keywords

1,2 DI(PROP 1 YNYL)ARENE; ALKYNE; ANNULENE DERIVATIVE; DEHYDROBENZANNULENE; POLYCYCLIC AROMATIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; MICROWAVE IRRADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0037238556     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

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37. 2: C, 14.78; H, 0.41. Found: C, 14.74; H, 0.04. (g) Garden, S. J.; Torres, J. C. Ferreira, A. A.; Silva, R. B.; Pinto, A. C. Tetrahedron Lett. 1997, 38, 1501. (h) Lisowski, V.; Robba, M.; Rault, S. J. Org. Chem. 2000, 65, 4193. (i) Nakayama, J.; Sakai, A.; Hoshino, M. J. Org. Chem. 1984, 49, 5084.
38. 2: C, 14.78; H, 0.41. Found: C, 14.74; H, 0.04. (g) Garden, S. J.; Torres, J. C. Ferreira, A. A.; Silva, R. B.; Pinto, A. C. Tetrahedron Lett. 1997, 38, 1501. (h) Lisowski, V.; Robba, M.; Rault, S. J. Org. Chem. 2000, 65, 4193. (i) Nakayama, J.; Sakai, A.; Hoshino, M. J. Org. Chem. 1984, 49, 5084.
39. 2: C, 14.78; H, 0.41. Found: C, 14.74; H, 0.04. (g) Garden, S. J.; Torres, J. C. Ferreira, A. A.; Silva, R. B.; Pinto, A. C. Tetrahedron Lett. 1997, 38, 1501. (h) Lisowski, V.; Robba, M.; Rault, S. J. Org. Chem. 2000, 65, 4193. (i) Nakayama, J.; Sakai, A.; Hoshino, M. J. Org. Chem. 1984, 49, 5084.
40. 2: C, 14.78; H, 0.41. Found: C, 14.74; H, 0.04. (g) Garden, S. J.; Torres, J. C. Ferreira, A. A.; Silva, R. B.; Pinto, A. C. Tetrahedron Lett. 1997, 38, 1501. (h) Lisowski, V.; Robba, M.; Rault, S. J. Org. Chem. 2000, 65, 4193. (i) Nakayama, J.; Sakai, A.; Hoshino, M. J. Org. Chem. 1984, 49, 5084.
41. 2: C, 14.78; H, 0.41. Found: C, 14.74; H, 0.04. (g) Garden, S. J.; Torres, J. C. Ferreira, A. A.; Silva, R. B.; Pinto, A. C. Tetrahedron Lett. 1997, 38, 1501. (h) Lisowski, V.; Robba, M.; Rault, S. J. Org. Chem. 2000, 65, 4193. (i) Nakayama, J.; Sakai, A.; Hoshino, M. J. Org. Chem. 1984, 49, 5084.
42. 2: C, 14.78; H, 0.41. Found: C, 14.74; H, 0.04. (g) Garden, S. J.; Torres, J. C. Ferreira, A. A.; Silva, R. B.; Pinto, A. C. Tetrahedron Lett. 1997, 38, 1501. (h) Lisowski, V.; Robba, M.; Rault, S. J. Org. Chem. 2000, 65, 4193. (i) Nakayama, J.; Sakai, A.; Hoshino, M. J. Org. Chem. 1984, 49, 5084.
43. 2: C, 14.78; H, 0.41. Found: C, 14.74; H, 0.04. (g) Garden, S. J.; Torres, J. C. Ferreira, A. A.; Silva, R. B.; Pinto, A. C. Tetrahedron Lett. 1997, 38, 1501. (h) Lisowski, V.; Robba, M.; Rault, S. J. Org. Chem. 2000, 65, 4193. (i) Nakayama, J.; Sakai, A.; Hoshino, M. J. Org. Chem. 1984, 49, 5084.
44. 2: C, 14.78; H, 0.41. Found: C, 14.74; H, 0.04. (g) Garden, S. J.; Torres, J. C. Ferreira, A. A.; Silva, R. B.; Pinto, A. C. Tetrahedron Lett. 1997, 38, 1501. (h) Lisowski, V.; Robba, M.; Rault, S. J. Org. Chem. 2000, 65, 4193. (i) Nakayama, J.; Sakai, A.; Hoshino, M. J. Org. Chem. 1984, 49, 5084.
45. 2: C, 14.78; H, 0.41. Found: C, 14.74; H, 0.04. (g) Garden, S. J.; Torres, J. C. Ferreira, A. A.; Silva, R. B.; Pinto, A. C. Tetrahedron Lett. 1997, 38, 1501. (h) Lisowski, V.; Robba, M.; Rault, S. J. Org. Chem. 2000, 65, 4193. (i) Nakayama, J.; Sakai, A.; Hoshino, M. J. Org. Chem. 1984, 49, 5084.
46. 4. Solvent was removed in vacuo and the resulting crude product purified by Kugelrohr distillation, sublimation, or chromatography.
47. (a) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: New York, 1998, Chap. 5.
48. (b) Sonogashira, K. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M., Ed.; Pergamon: New York, 1991, Chap. 2.4.
49. A somewhat related application of microwaves in Sonogashira reactions is described in: Erdelyi, M.; Gogoll, A. J. Org. Chem. 2001, 66, 4165.
50. Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
51. 2 (19.6 mg, 0.028 mmol), CuI (5.4 mg, 0.028 mmol), and the dibromodiiodobenzene (0.113 mmol). The vial was sealed, evacuated, and filled with propyne through a Teflon septum up to 2.5 atm pressure. It was then irradiated in a Smith Synthesizer single-mode microwave cavity, producing continuous radiation at 2450 MHz. The resulting solution was immediately filtered through a short plug of silica gel (hexanes/ethyl acetate) to remove the catalyst and the crude product further purified by column chromatography on silica gel (hexanes).
52. (a) Iyoda, M.; Vorasingha, A.; Kuwatani, Y.; Yoshida, M. Tetrahedron Lett. 1998, 39, 4701.
53. (b) Huynh, C.; Linstrumelle, G. Tetrahedron 1988, 44, 6337.
54. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, 1987, Chap. 9.
55. 18: 522.1408. Found: 522.1428.
56. The spectral data are in good agreement with those in: Staab, H. A.; Graf, F. Chem. Ber. 1970, 103, 1107.
57. 17a
58. Srinivasan, M.; Sankararaman, S.; Dix, I.; Jones, P. G. Org. Lett. 2000, 2, 3849.
59. (a) Alkorta, I.; Rozas, I.; Elguero, J. Tetrahedron 2001, 57, 6043.
60. (b) Jusélius, J.; Sundholm, D. Phys. Chem. 2001, 3, 2433.
61. (c) Godard, C.; Lepetit, C.; Chauvin, R. Chem. Commun. 2000, 1833.
62. (d) Wan, W. B.; Kimball, D. B.; Haley, M. M. Tetrahedron Lett. 1998, 39, 6795.
63. (e) Matzger, A. J.; Vollhardt, K. P. C. Tetrahedron Lett. 1998, 39, 6791.
64. Details of the crystal structure determination (deposition number CCDC 192630) may be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk].