Synthesis of biindolyls via palladium-catalyzed reactions

Journal of Organic Chemistry

Volumn 73, Issue 22, 2008, Pages 9177-9180

  Duong, Hung A ^a   Chua, Sheena ^a   Huleatt, Paul B ^a   Chai, Christina L L ^a  

^a INSTITUTE OF CHEMICAL AND ENGINEERING SCIENCES   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; CHEMICAL REACTIONS; PALLADIUM;

BORYLATION; CATALYZED REACTIONS; CHEMICAL EQUATIONS; ONE POTS; STERICALLY CONGESTED; SYNTHESIS OF;

SYNTHESIS (CHEMICAL);

BORONIC ACID DERIVATIVE; CARBON; DIMETHYL 5,5',6,6' TETRAMETHOXY 1H 1'H 7,7' BIINDOLE 2,2' DICARBOXYLATE; INDOLE DERIVATIVE; METHYL 3 (2 (METHOXYCARBONYL) 1 BENZYL 5,6 DIMETHOXY 1H INDOL 3 YL) 1 BENZYL 5,6 DIMETHOXY 1H INDOLE 2 CARBOXYLATE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; DECARBOXYLATION; DIMERIZATION; ONE POT SYNTHESIS; SAPONIFICATION; SUZUKI REACTION;

BORONIC ACIDS; CATALYSIS; INDICATORS AND REAGENTS; INDOLES; LIGANDS; PALLADIUM; SOLVENTS;

EID: 56449120611     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801846b     Document Type: Article

References (49)

1. (a) Evans, B. E.; Rittle, K. E.; Bock, M. G.; Dipardo, R. M.; Freidinger, R. M.; Whitter, W. L.; Lundell, G. F.; Verber, D. F.; Anderson, P. S.; Chang, R. S. L.; Lotti, V. J.; Cerino, D. H.; Chen, T. B.; Kling, P. J.; Kunkel, K. A.; Springer, J. P.; Hirshfield, J. J. Med. Chem. 1988, 31, 2235.
2. (b) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev 2003, 103, 893, and references cited therein.
3. Bringmann, G.; Mortimer, A. J. P.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem., Int. Ed. 2005, 44, 5384.
4. (a) Berens, U.; Brown, J. M.; Long, J.; Selke, R. Tetrahedron: Asymmetry 1996, 7, 285.
5. (b) Benincori, T.; Piccolo, O.; Rizzo, S.; Sannicolo, F. J. Org. Chem. 2000, 65, 8340.
6. (c) McCormick, T. M.; Liu, Q.; Wang, S. Org. Lett. 2007, 9, 4087.
7. (a) Prota, G. Melanins and Melanogenesis; Academic: San Diego, CA, 1992.
8. (b) Prota, G. Fortschr. Chem. Org. Naturst. 1995, 64, 93.
9. (c) Prota, G.; Thomson, R. H. Endeavour 1976, 35, 32.
10. (d) Kollias, N.; Sayre, R. M.; Zeise, L.; Chedekel, M. R. Photochem. Photobiol. 1991, 9, 135.
11. (e) Riley, P. A. Int. J. Biochem. Cell Biol. 1997, 29, 1235.
12. (f) Krol, E. S.; Liebler, D. C. Chem. Res. Toxicol. 1998, 11, 1434.
13. (a) d'Ischia, M.; Napolitano, A.; Tsiakas, K.; Prota, G. Tetrahedron 1990, 46, 5789.
14. (b) Pezzella, A.; Panzella, L.; Natangelo, A.; Arzillo, M.; Napolitano, A.; d'Ischia, M. J. Org. Chem. 2007, 72, 9225.
15. (c) Pezzella, A.; Crescenzi, O.; Natangelo, A.; Panzella, L.; Napolitano, A.; Navaratnam, S.; Edge, R.; Land, E. J.; Barone, V.; d'Ischia, M. J. Org. Chem. 2007, 72, 1595.
16. (d) d'Ischia, M.; Crescenzi, O.; Pezzella, A.; Arzillo, M.; Panzella, L.; Napolitano, A.; Barone, V. Photochem. Photobiol. 2008, 84, 600.
17. (a) Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 36, 3437.
18. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
19. (c) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
20. (a) Matteson, D. S. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; Wiley: New York, 1987; Vol. 4, p 307.
21. (b) Vaultier, M.; Carboni, B. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, UK, 1995; Vol. 11, pp 191.
22. (c) Miyaura, N.; Marouka, K. In Synthesis of Organometallic Compounds; Komiya, S., Ed.; Wiley: New York, 1997; p 345.
23. (a) Ishiyama, T.; Takagi, J.; Hartwig, J. F.; Miyaura, N. Angew. Chem., Int. Ed. 2002, 41, 16.
24. (b) Takagi, J.; Sato, K.; Hartwig, J. F.; Ishiyama, T.; Miyaura, N. Tetrahedron Lett. 2002, 43, 5649.
25. Paul, S.; Chotana, G. A.; Holmes, D.; Reichle, R. C.; Maleczka, R. E.; Smith, M. R. J. Am. Chem. Soc. 2006, 128, 15552.
26. (a) Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508.
27. (b) Ishiyama, T.; Itoh, Y.; Kitano, T.; Miyaura, N. Tetrahedron Lett. 1997, 38, 3447.
28. (c) Murata, M.; Watanabe, S.; Masuda, Y. J. Org. Chem. 1997, 62, 6458.
29. (d) Baudoin, O.; Guenard, D.; Gueritte, F. J. Org. Chem. 2000, 65, 9268.
30. (e) Murata, M.; Oyama, T.; Watanabe, S.; Masuda, Y. J. Org. Chem. 2000, 65, 164.
31. (f) Murata, M.; Sambommatsu, T.; Watanabe, S.; Masuda, Y. Synlett 2006, 12, 1867.
32. Barder, T. E.; Walker, S. D.; Joseph, R. M.; Buehwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
33. Billingsley, K.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3358.
34. For examples on the synthesis of biindolyls, see: (a) Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1997, 62, 2312.
35. (b) Merlic, C. A.; McInnes, D. M. Tetrahedron. Lett. 1997, 38, 7661.
36. (c) Kuethe, J. T.; Wong, A.; Davies, I. W. Org. Lett. 2003, 5, 3721.
37. (d) Hee, S. P. H.; Lee, V.; Baldwin, J. E.; Cowley, A. Tetrahedron 2004, 60, 3695.
38. (e) Jones, A. W.; Wahyuningsih, T. D.; Pchalek, K.; Kumar, N.; Black, D. S. Tetrahedron 2005, 61, 10490.
39. (f) Rempel, S. P. N.; Olsen, S.; Mahadevan, I. B.; Netchev, G.; Wilson, B. C.; Smith, S. C.; Dunlop, H. R.; Meredith, P. Photochem. Photobiol. 2008, 84, 613.
40. For examples on the preparation of symmetrical biaryls via one-pot borylation and subsequent Suzuki-Miyaura reaction, see: (a) Baudoin, O.; Cesario, M.; Guenard, D.; Gueritte, F. J. Org. Chem. 2002, 67, 1199.
41. (b) Nising, C. F.; Schmid, U. K.; Nieger, M.; Brase, S. J. Org. Chem. 2004, 69, 6830.
42. (c) Broutin, P. E.; Cerna, I.; Campaniello, I. M.; Leroux, F.; Colobert, F. Org. Lett. 2004, 6, 4419.
43. (d) Hashim, J.; Glasnov, T. N.; Kremsner, J. M.; Kappe, C. O. J. Org. Chem. 2006, 71, 1707.
44. (e) Billingsle, K. L.; Barder, T. E.; Buchwald, S. L. Angew. Chem., Int. Ed. 2007, 46, 5359.
45. (f) Kikuchi, T.; Nobuta, Y.; Umeda, J.; Yamamoto, Y.; Ishiyama, T.; Miyaura, N. Tetrahedron 2008, 22, 4967.
46. Huleatt, P. B.; Choo, S. S.; Chua, S.; Chai, C. L. L. Tetrahedron Lett. 2008, 49, 5309.
47. Wallace, T. W. Org. Biomol. Chem. 2006, 4, 3197.
48. Mentzel, U. V.; Tanner, D.; Tonder, J. E. J. Org. Chem. 2006, 71, 5807.
49. Handy, S. T.; Bregman, H.; Lewis, J.; Zhang, X.; Zhang, Y. Tetrahedron Lett. 2003, 44, 427.