Photoinduced rearrangements of 3,3′-bis(arylbenzofurans)

Organic Letters

Volumn 13, Issue 3, 2011, Pages 474-477

  Auzias, Mathieu ^a   Häussinger, Daniel ^a   Neuburger, Markus ^a   Wegner, Hermann A ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; ETHYLENE DERIVATIVE; FUSED HETEROCYCLIC RINGS; NITRILE; TETRACYANOETHYLENE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; PHOTOCHEMISTRY; SYNTHESIS;

BENZOFURANS; COMBINATORIAL CHEMISTRY TECHNIQUES; ETHYLENES; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MOLECULAR STRUCTURE; NITRILES; PHOTOCHEMICAL PROCESSES;

EID: 79851489429     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102816a     Document Type: Article

References (42)

1. Roth, H. D. Angrew. Chem. Int. Ed. Engl. 1989, 28, 1193.
2. Hoffmann, N. Chem. Rev. 2008, 108, 1052.
3. Ciana, C.-L.; Bochet, C. G. Chimia 2007, 61, 650.
4. For recent selected examples see: (a) Ravelli, D.; Zema, M.; Mella, M.; Fagnoni, M.; Albini, A. Org. Biomol. Chem. 2010, 8, 4158.
5. (b) Fasani, E.; Manet, I.; Capobianco, M. L.; Monti, S.; Pretali, L.; Albini, A. Org. Biomol. Chem. 2010, 8, 3621.
6. (c) Fleck, M.; Bach, T. Chem.-Eur. J. 2010, 16, 6015.
7. (d) Jahjah, R.; Gassama, A.; Bulach, V.; Suzuki, C.; Abe, M.; Hoffmann, N.; Martinez, A.; Nuzillard, J.-M. Chem.-Eur. J. 2010, 16, 3341.
8. (e) Dichiarante, V.; Fagnoni, M.; Albini, A. Green Chem. 2009, 11, 942.
9. (f) Selig, P.; Herdtweck, E.; Bach, T. Chem.-Eur. J. 2009, 15, 3509.
10. (g) Griesbeck, A. G.; Neudörfl, J.; Hörauf, A.; Specht, S.; Raabe, A. J. Med. Chem. 2009, 52, 3420.
11. (h) Vogt, F.; Jödicke, K.; Schröder, J.; Bach, T. Synthesis 2009, 4268.
12. (i) Débieux, J. L.; Bochet, C. G. J. Org. Chem. 2009, 74, 4519.
13. (j) Zimmerman, H. E.; Shorunov, S. J. Org. Chem. 2009, 74, 5411.
14. (k) Fleck, M.; Bach, T. Angew. Chem., Int. Ed. 2008, 47, 6189.
15. (l) Guthmann, H.; Könemann, M.; Bach, T. Eur. J. Org. Chem. 2007, 632.
16. (m) Bauer, A.; Westkämper, F.; Grimme, S.; Bach, T. Nature 2005, 436, 1139.
17. (a) Yamaguchi, T.; Takami, S.; Irie, M. J. Photochem. Photobiol., A 2008, 193, 146.
18. (b) Sakamoto, M.; Kinbara, A.; Yagi, T.; Mino, T.; Yamaguchi K.; Fujita, T. Chem. Commun. 2000, 1201.
19. (a) Škoriæ, I.; Ciorba, S.; Spalletti, A.; Šindler-Kulyk, M. J. Photochem. Photobiol, A 2009, 202, 136.
20. (b) Piloto, A. M.; Fonseca, A. S. C.; Costa, S. P. G.; Gonçalves, M. S. T. Tetrahedron 2006, 62, 9258.
21. (c) Piloto, A. M.; Costa, S. P. G.; Gonçalves, M. S. T. Tetrahedron Lett. 2005, 46, 4757.
22. Anderson, S.; Taylor, P. N.; Verschoor, G. L. B. Chem.-Eur. J. 2004, 10, 518.
23. Auzias, M. G.; Neuburger, M.; Wegner, H. A. Synlett 2010, 16, 2443.
24. UV lamp 254/302/365 nm, UVProducts.
25. UV Monochromator, Polychrome V, Till Photonics.
26. Rayonet reactor RPR-100, Southern New England Ultra Violet Company, 270/300/350 nm.
27. Similar benzonaphthofurans have been synthesized recently by the halopalladation/decarboxylation/carbon-carbon bond forming domino process in moderate to good yields: Huang, X.-C.; Wang, F.; Liang, Y.; Li, J.-H. Qrg. Lett. 2009, 11, 1139.
28. (a) Clennan, E. L. Tetrahedron 2000, 56, 9151.
29. (b) Prein, M.; Adam, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 477.
30. (c) Prein, M.; Adam, W. Acc. Chem. Res. 1996, 29, 275.
31. (d) Schweitzer, C.; Schmidt, R. Chem. Rev. 2003, 103, 1685.
32. (e) For examples of organic chemistry of singlet oxygen see: Tetrahedron 2006, 62, 46.
33. (a) Clenann, E. L. In Molecular and Supramolecular Photochemistry; Ramamurthy, V., Schanze, K. S., Eds.; Vol. 12, Synthetic Organic Photochemistry; Griesbeck, A. G., Mattay, J., Eds.; Marcel Dekker: New York, 2005; p 365.
34. (b) Stratakis, M.; Orfanopoulos, M. Tetrahedron 2000, 56, 1595.
35. (c) Adam, W.; Wirth, T. Acc. Chem,. Res. 1999, 32, 703.
36. (a) Miller, J. S. Angew. Chem., Int. Ed. 2006, 45, 2508.
37. (b) Linn, W. J. Org. Synth. 1969, 49, 103.
38. Phelan, N. F.; Orchim, M. J. Chem. Educ. 1968, 45, 633.
39. Gholami, M.; Tykwinski, R. R. Chem. Rev. 2006, 106, 4997.
40. (a) Naef, R. Dyes Pigm. 1991, 17, 113.
41. (b) Klessinger, M. Dyes Pigm. 1982, 3, 235.
42. Francolini, I.; Norris, P.; Piozzi, A.; Donelli, G.; Stoodley, P. Antimicrob. Agents Chemother. 2004, 48, 4360.