A versatile preparation of geländer-type p-terphenyls from a readily available diacetylenic precursor

Organic Letters

Volumn 11, Issue 20, 2009, Pages 4656-4659

  Modjewski, Matthew ^a   Lindeman, Sergey V ^a   Rathore, Rajendra ^a  

^a Marquette University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 70349902454     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901938f     Document Type: Article

References (21)

1. (a) Kiupel, B.; Niederalt, C.: Nieger, M.: Grimme. S.; Vogtle, F. Angew. Chem., Int. Ed. 1998, 37, 3031-3034.
2. (b) Grimme, S.: Harren. J.; Sobanski, A.; Vogtle, F. Eur. J. Org. Chem. 1998, 149, 1-1509.
3. (c) Also see :Hill, D. J.: Mio, M. J.; Prince, R. B.: Hughes, T. S.: Moore, J. S. Chem. Rev. 2001. 101, 3893-4011.
4. (a) Koěovský, P.; Vyskočil, S.: Smrèina, M. Chem. Rev. 2003, 103, 3213-3245.
5. (b) Jeulin, S.: de Paule, S. D.; Ratovelomanana-VidaL V.; Genêt, J.-P.; Champion, N.: Dellis, P. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5799-5804.
6. (c) Vachon. J.; Perollier, C.; Monchaud. D.: Marsol, C.: Ditrich, K.; Lacour, J. J. Org. Chem. 2005, 70, 5903-5911.
7. (d) Goncalves-Farbos. M.-H.: Vial. L.; Lacour, J. Chem. Commun. 2008, 829-831, and references cited therein.
8. (a) Griffin, G. W.; Horn, K. A. Org. Prep. Proc. Int. 1985, 17, 187-190.
9. (b) Muellen, K.; Heinz, W.; Klaemer. F. G.: Roth. W. R.; Kindermann. I.; Adamczak, O.; Wette, M.; Lex, J. Chem. Ber. 1990, 123, 2349-2371.
10. (c) Pomerantz. M.; Dassanayake. N. L.; McManus, T. R.; Reynolds, C. H. J. Org. Chem. 1984, 49, 4029-4032.
11. (a) Jaime, C.; Font, J. J. Org. Chem. 1990, 55, 2637-2644.
12. (b) Mislow, K.: Glass, M. A. W.; Hopps, H. B.; Simon. E.; Wahl, G. H., Jr. J. Am. Chem. Soc. 1964, 86, 1710-1733.
13. Sonogashira, K. In Comprehensive Organic Synthesis: Trost, B. M. Fleming, I., Eds.; Pergamon: Oxford, 1991: Vol.3, pp 521-548.
14. l,4-Dibromo-2,5-diiodobenzene is commercially available and can also be easily prepared from 1,4-dibromobenzene. See: Chanteau, S. H,: Tour, J. M. J. Org. Chem. 2003, 68, 8750-8766.
15. (a) Suzuki, A. Chem. Commun. 2005, 4759-4763.
16. (b) Hassan. J.: Sevignon, M.: Gozzi. C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1469, and references therein.
17. Compare: Rathore, R.: Abdelwahed, S. H.: Guzei. I. A. J. Am. Chem. Soc. 2003, 125, 8712.
18. Rathore, R.; Burns. C. L. J. Org. Chem. 2003, 68, 4071-4074.
19. The DFT calculations were performed using Spartan 10.
20. Franco, G.; Alberti, A.; Guerra, M.; Seconi, G.; Vivarelli, P. Compare. J. Chem. Soc., Perkin Trans. 2 1976, 173-178, and references cited therein.
21. Banerjee, M.; Shukla, R.; Rathore, R. J. Am. Chem. Soc. 2009, 131, 1780-1786, and references cited therein.