Synthesis of higher helicenes via olefin metathesis and C-H activation

Synthesis

Volumn , Issue 9, 2009, Pages 1499-1505

  Côté, Julie ^a   Collins, Shawn K ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

Arylation; C H activation; Helicene; Heterohelicene; Olefin metathesis

Indexed keywords

ARYLATION; C-H ACTIVATION; HELICENE; HETEROHELICENE; OLEFIN METATHESIS;

ACTIVATION ANALYSIS; OLEFINS; ORGANIC SOLVENTS; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

ALKENE; CARBON; HETEROHELICENE DERIVATIVE; HYDROGEN; POLYCYCLIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CHEMICAL BOND; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DECOMPOSITION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; SOLUBILITY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 67650089596     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1088165     Document Type: Article

References (58)

1. (a) Schmuck, C. Angew. Chem. Int. Ed. 2003, 42, 2448.
2. (b) Hopf, H. Classics in Hydrocarbon Chemistry; Wiley-VCH: Weinheim, 2000, 321-330.
3. (c) Vögtle, F. Fascinating Molecules in Organic Chemistry; Wiley: New York, 1992, 156-180.
4. (d) Meurer, K. P.; Vögtle, F. Top. Curr. Chem. 1985, 127, 1.
5. (e) For some examples of optical or electronic properties of helicenes see: Martin, R. H. Angew. Chem., Int. Ed. Engl. 1974, 13, 649.
6. (f) Hu, Y.; Wex, B.; Perkovic, M. W.; Neckers, D. C. Tetrahedron 2008, 64, 2251.
7. (g) Katz, T. J. Angew. Chem. Int. Ed. 2000, 39, 1921.
8. (h) For examples of medicinal properties see: Grimme, S.; Harren, L.; Sobanski, A.; Vögtle, F. Eur. J. Org. Chem. 1998, 1491.
9. (i) Honzawa, S.; Okubo, H.; Anzai, S.; Yamaguchi, M.; Tsumoto, K.; Kumagai, I. Bioorg. Med. Chem. 2002, 10, 3213.
10. (j) Xu, Y.; Zhang, X. Y.; Sugiyama, H.; Umano, T.; Osuga, H.; Tanaka, K. J. Am. Chem. Soc. 2004, 126, 6566.
11. For a recent review of helicene synthesis see: (a) For other recent examples see: Urbano, A. Angew. Chem. Int. Ed. 2003, 42, 3986.
12. (b) Harrowven, D. C.; Guy, I. L.; Nanson, L. Angew. Chem. Int. Ed. 2006, 45, 2242.
13. (c) Dubois, F.; Gingras, M. Tetrahedron Lett. 1998, 39, 5039.
14. (d) Zhang, Y.; Petersen, J. L.; Wang, K. K. Tetrahedron 2008, 64, 1285.
15. (e) Rajca, A.; Rajca, S.; Pink, M.; Miyasaka, M. Synlett 2007, 1799.
16. (f) Ichikawa, J.; Yokota, M.; Kudo, T.; Umezaki, S. Angew. Chem. Int. Ed. 2008, 47, 4870.
17. (a) Kagan, H.; Moradpour, A.; Nicoud, J. F.; Balavoine, G.; Martin, R. H.; Cosyn, J. P. Tetrahedron Lett. 1971, 12, 2479.
18. (b) Martin, R. H.; Baes, M. Tetrahedron 1975, 31, 2135.
19. (c) Moradpour, A.; Kagan, H.; Baes, M.; Morren, G.; Martin, R. H. Tetrahedron 1975, 31, 2139.
20. (d) Martin, R. H.; Morren, G.; Schurter, J. J. Tetrahedron Lett. 1969, 10, 3683.
21. (a) Carreno, M. C.; Gonzalez-Lopez, M.; Urbano, A. Chem. Commun. 2005, 611.
22. (b) Carreno, M. C.; Garcia-Cerrada, S.; Urbano, A. Chem.-Eur. J. 2003, 9, 4118.
23. (c) Carreno, M. C.; Garcia-Cerrada, S.; Urbano, A. J. Am. Chem. Soc. 2001, 123, 7929.
24. (d) Paruch, K.; Vyklicky, L.; Katz, T. J. Org. Synth. 2003, 80, 233.
25. (e) Paruch, K.; Vyklicky, L.; David, Z.; Katz, T. J.; Incarvito, C.; Zakharov, L.; Rheingold, A. L. J. Org. Chem. 2003, 68, 8539.
26. (f) Willmore, N. D.; Liu, L.; Katz, T. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1093.
27. (g) Carreno, M. C.; Enriquez, A.; Garcia-Cerrada, S.; Sanz-Cuesta, M. J.; Urbano, A.; Maseras, F.; Nonell-Canals, A. Chem.-Eur. J. 2008, 14, 603.
28. For the use of [2+2+2] cycloadditions to access helicenes see: (a) Míšek, J.; Teplý, F.; Stará, I. G.; Tichý, M.; Šaman, D.; Císařová, I.; Vojtíšek, P.; Starý, I. Angew. Chem. Int. Ed. 2008, 47, 3188.
29. (b) Stará, I. G.; Starý, I.; Kollárovic, A.; Teplý, F.; Vyskočil, ; Šaman, D. Tetrahedron Lett. 1999, 40, 1993.
30. (c) Teplý, F.; Stará, I. G.; Starý, I.; Kollárovic, A.; Šaman, D.; Rulíšek, L.; Fiedler, P. J. Am. Chem. Soc. 2002, 124, 9175.
31. (d) Sehnal, P.; Krausova, Z.; Teply, F.; Stara, I. G.; Stary, I.; Rulisek, L.; Saman, D.; Cisarova, I. J. Org. Chem. 2008, 73, 2074.
32. (e) Stary, I.; Stara, I. G.; Alexandrova, Z.; Sehnal, P.; Teply, F.; Saman, D.; Rulisek, L. Pure Appl. Chem. 2006, 78, 495.
33. (f) Stara, I. G.; Alexandrova, Z.; Teply, F.; Sehnal, P.; Stary, I.; Saman, D.; Budesinsky, M.; Cvacka, J. Org. Lett. 2005, 7, 2547.
34. (g) Tanaka, K.; Kamisawa, A.; Suda, T.; Noguchi, K.; Hirano, M. J. Am. Chem. Soc. 2007, 129, 12078.
35. Collins, S. K.; Grandbois, A.; Vachon, M. P.; Côté, J. Angew. Chem. Int. Ed. 2006, 45, 2923.
36. For other recent examples of the asymmetric synthesis of heterohelicenes see: (a) Rajca, A.; Miyasaka, M.; Pink, M.; Wang, H.; Rajca, S. J. Am. Chem. Soc. 2004, 126, 15211.
37. (b) Nakano, K.; Hidehira, Y.; Takahashi, K.; Hiyama, T.; Nozaki, K. Angew. Chem. Int. Ed. 2005, 44, 7136.
38. (c) Lamanna, G.; Faggi, C.; Gasparrini, F.; Ciogli, A.; Villani, C.; Stephens, P. J.; Devlin, F. J.; Menichetti, S. Chem.-Eur. J. 2008, 14, 5747.
39. For some recent reviews/highlights in arylation see: (a) Lewis, J. C.; Berman, A. M.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 2493.
40. (b) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
41. (c) Campeau, L.-C.; Stuart, D. R.; Fagnou, K. Aldrichimica Acta 2007, 40, 35.
42. (d) Yanagisawa, S.; Sudo, T.; Noyori, R.; Itami, K. J. Am. Chem. Soc. 2006, 128, 11748.
43. (e) Deprez, N. R.; Kalyani, D.; Krause, A.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 4972.
44. (f) Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 11904.
45. For a recent example of helicenes with aryl groups at the interior positions see: Hu, Y.; Wex, B.; Perkovic, M. W.; Neckers, D. C. Tetrahedron 2008, 64, 2251.
46. For another example of the use of similar silver(I) salts see: Jung, M. E.; Nichols, C. J. J. Org. Chem. 1998, 63, 347.
47. (a) Campeau, L.-C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581.
48. (b) Campeau, L.-C.; Thansandote, P.; Fagnou, K. Org. Lett. 2005, 7, 1857.
49. Attempts to invert the sequence and perform arylation on 9 prior to metathesis gave only complex product mixtures.
50. (a) Lafrance, M.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 16496.
51. (b) Oezdemir, I.; Demir, S.; Cetinkaya, B.; Gourlaouen, C.; Maseras, F.; Bruneau, C.; Dixneuf, P. H. J. Am. Chem. Soc. 2008, 130, 1156.
52. The analogous bromide and iodide of 2 also gave 5 as the major product.
53. Kamikawa, K.; Takemoto, I.; Takemoto, S.; Matsuzaka, H. J. Org. Chem. 2007, 72, 7406.
54. X-ray crystal structure data have been deposited at the Cambridge Crystallographic Data Centre under reference numbers CCDC-723431 (5), CCDC-723433 (10), and CCDC-723432 (24a). These data can be obtained free of charge at www.ccdc.com.ac.uk or from CCDC, 12, Union Road, Cambridge CB2 1EK, UK; fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk.
55. 3 centers see: (a) Campeau, L.-C.; Schipper, D. J.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 3266.
56. (b) Mousseau, J. J.; Larivee, A.; Charette, A. B. Org. Lett. 2008, 10, 1641.
57. Lee, E.; Huang, Z.; Ryu, J.-H.; Lee, M. Chem.-Eur. J. 2008, 14, 6957.
58. Lee, E.; Kim, J.-K.; Lee, M. Angew. Chem. Int. Ed. 2008, 47, 6375.