Selenium-mediated synthesis of biaryls through rearrangement

Organic Letters

Volumn 12, Issue 6, 2010, Pages 1364-1367

  Shahzad, Sohail A ^a   Vivant, Clotilde ^a   Wirth, Thomas ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77949841964     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100274e     Document Type: Article

References (31)

1. Freudendahl, D. M.; Shahzad, S. A.; Wirth, T. Eur. J. Org. Chem. 2009, 1649.
2. For a review, see: Tiecco, M. Top. Curr. Chem. 2000, 208, 7.
3. (a) Jackson, W. P.; Ley, S. V.; Whittle, A. J. J. Chem. Soc., Chem. Commun. 1980, 1173.
4. (b) Cuñat, A. C.; Dáez-Martán, D.; Ley, S. V.; Montgomery, F. J. J. Chem. Soc., Perkin Trans. 1 1996, 611.
5. (c) Worlikar, S. A.; Kesharwani, T.; Yao, T.; Larock, R. C. J. Org. Chem. 2007, 72, 1347.
6. Huang, X.; Xue, J. J. Org. Chem. 2007, 72, 3965, and references therein.
7. (a) Hasegawa, M.; Takenouchi, K.; Takahashi, K.; Takeuchi, T.; Komoriya, K.; Uejima, Y.; Kamimura, T. J. Med. Chem. 1997, 40, 395.
8. (b) Pathak, A.; Kulshreshtha, D. K.; Maurya, R. Phytochemistry 2004, 65, 2153.
9. (c) Demirezer, Ö .; Kuruüzüm, A.; Bergere, I.; Schiewe, H.-J.; Zeeck, A. Phytochemistry 2001, 56, 399.
10. (d) Gondo, M.; Tanaka, N.; Tanaka, T.; Shimomura, K.; Nakanishi, F.; Ishimaru, K. Phytochemistry 1999, 51, 879.
11. (e) Thomson, R. H. Naturally Occuring Quinones IV. Recent Advances, 4th ed.; Chapman & Hall: London, 1997.
12. (f) Bringmann, G.; Günther, G.; Ochse, M.; Schupp, O.; Tasler, S. In Progress in the Chemistry of Organic Natural Products; Herz, W., Falk, H., Kirby, G. W., Moore, R. E., Tamm, C., Eds.; Springer: New York, 2001; Vol.82, 1.
13. (g) Bonesi, S. M.; Fagnoni, M.; Albini, A. Angew. Chem., Int. Ed. 2008, 47, 10022.
14. (a) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977.
15. (b) Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40.
16. (c) Noyori, R.; Yamakawa, M.; Hashiguchi, S. J. Org. Chem. 2001, 66, 7931.
17. (d) Kumobayashi, H.; Miura, T.; Sayo, N.; Saito, T.; Zhang, X. Synlett 2001, 1055.
18. (e) Bringmann, G.; Mortimer, A. J. P.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem., Int. Ed. 2005, 44, 5384.
19. (f) Kozlowski, M. C.; Morgan, B. J.; Linton, E. C. Chem. Soc. Rev. 2009, 38, 3193.
20. Shahzad, S. A; Wirth, T. Angew. Chem. 2009, 121, 2626;
21. Angew. Chem., Int. Ed. 2009, 48, 2588.
22. Taylor, G. A. J. Chem. Soc., Perkin Trans. 1 1981, 3132.
23. CCDC-760701 (5a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc-.cam.ac.uk/ conts/retrieving.html (or from the CCDC, 12 Union Road, CambridgeCB21EZ,UK;fax: +441223336033;ore-mail:deposit@ccdc.cam.ac.uk).
24. (a) de Koning, C. B.; Rousseau, A. L.; van Otterlo, W. A. L. Tetrahedron 2003, 59, 7.
25. (b) Karady, S.; Amato, J. S.; Reamer, R. A.; Weinstock, L. M. Tetrahedron Lett. 1996, 37, 8277.
26. (a) Ciufolini, M. A.; Weiss, T. J. Tetrahedron Lett. 1994, 35, 1127.
27. (b) Belmont, P.; Andrez, J. C.; Allan, C. S. M. Tetrahedron Lett. 2004, 45, 2783.
28. (c) Belmont, P.; Parker, E. Eur. J. Org. Chem. 2009, 6075.
29. Browne, D. M.; Niyomura, O.; Wirth, T. Org. Lett. 2007, 9, 3169.
30. Frisch, M. J. ; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G. ; Montgomery, J. A., Jr.; Stratmann, R. E. ; Burant, J. C. ; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; AlLaham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 03, revision B.04; Gaussian, Inc.: Wallingford, CT, 2004.
31. Boye, A. C.; Meyer, D.; Ingison, C. K.; French, A. N.; Wirth, T. Org. Lett. 2003, 5, 2157.