Platinum-catalyzed tandem indole annulation/arylation for the synthesis of diindolylmethanes and indolo[3,2-b ]carbazoles

Organic Letters

Volumn 15, Issue 16, 2013, Pages 4162-4165

  Shu, Dongxu ^a   Winston Mcpherson, Gabrielle N ^a   Song, Wangze ^a   Tang, Weiping ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CARBAZOLE DERIVATIVE; DIINDOLYLMETHANE; ETHER DERIVATIVE; INDOLE DERIVATIVE; PLATINUM; PROPARGYL ETHER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALKYNES; CARBAZOLES; CATALYSIS; CYCLIZATION; ETHERS; INDOLES; MOLECULAR STRUCTURE; PLATINUM;

EID: 84882801431     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4018408     Document Type: Article

References (35)

1. Barluenga, J.; Rodriguez, F.; Fananas, F. J. Chem.-Asian J. 2009, 4, 1036
2. Taber, D. F.; Tirunahari, P. K. Tetrahedron 2011, 67, 7195
3. Vicente, R. Org. Biomol. Chem. 2011, 9, 6469
4. Platon, M.; Amardeil, R.; Djakovitch, L.; Hierso, J.-C. Chem. Soc. Rev. 2012, 41, 3929
5. Cui, X.; Li, J.; Fu, Y.; Liu, L.; Guo, Q.-X. Tetrahedron Lett. 2008, 49, 3458
6. Oda, Y.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2012, 14, 664
7. Ackermann, L.; Lygin, A. V. Org. Lett. 2012, 14, 764
8. Inamoto, K.; Asano, N.; Nakamura, Y.; Yonemoto, M.; Kondo, Y. Org. Lett. 2012, 14, 2622
9. Xia, X.-F.; Wang, N.; Zhang, L.-L.; Song, X.-R.; Liu, X.-Y.; Liang, Y.-M. J. Org. Chem. 2012, 77, 9163
10. Song, W.; Ackermann, L. Chem. Commun. 2013, 49, 6638
11. Shu, D.; Song, W.; Li, X.; Tang, W. Angew. Chem., Int. Ed. 2013, 52, 3237
12. Han, X.; Li, H.; Hughes, R. P.; Wu, J. Angew. Chem., Int. Ed. 2012, 51, 10390
13. Wille, G.; Mayser, P.; Thoma, W.; Monsees, T.; Baumgart, A.; Schmitz, H. J.; Schrenk, D.; Polborn, K.; Steglich, W. Bioorg. Med. Chem. 2001, 9, 955
14. Kramer, H. J.; Podobinska, M.; Bartsch, A.; Battmann, A.; Thoma, W.; Bernd, A.; Kummer, W.; Irlinger, B.; Steglich, W.; Mayser, P. ChemBioChem 2005, 6, 860
15. Wahlstrom, N.; Romero, I.; Bergman, J. Eur. J. Org. Chem. 2004, 2593
16. Knolker, H. J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303
17. Schmidt, A. W.; Reddy, K. R.; Knoelker, H.-J. Chem. Rev. 2012, 112, 3193
18. Denison, M. S.; Soshilov, A. A.; He, G.; Degroot, D. E.; Zhao, B. Toxicol. Sci. 2011, 124, 1
19. Quintana, F. J.; Basso, A. S.; Iglesias, A. H.; Korn, T.; Farez, M. F.; Bettelli, E.; Caccamo, M.; Oukka, M.; Weiner, H. L. Nature 2008, 453, 65
20. Stevens, E. A.; Mezrich, J. D.; Bradfield, C. A. Immunology 2009, 127, 299
21. Li, Y.; Innocentin, S.; Withers, D. R.; Roberts, N. A.; Gallagher, A. R.; Grigorieva, E. F.; Wilhelm, C.; Veldhoen, M. Cell 2011, 147, 629
22. Kiss, E. A.; Vonarbourg, C.; Kopfmann, S.; Hobeika, E.; Finke, D.; Esser, C.; Diefenbach, A. Science 2011, 334, 1561
23. Mehta, V.; Vezina, C. M. Differentiation 2011, 82, 211
24. Fritz, W. A.; Lin, T.-M.; Safe, S.; Moore, R. W.; Peterson, R. E. Biochem. Pharmacol. 2009, 77, 1151
25. Jeong, K.-T.; Hwang, S.-J.; Oh, G.-S.; Park, J.-H. Int. Immunopharmacol. 2012, 13, 377
26. Gu, R.; Robeyns, K.; Van Meervelt, L.; Toppet, S.; Dehaen, W. Org. Biomol. Chem. 2008, 6, 2484
27. Boudreault, P. L. T.; Wakim, S.; Tang, M. L.; Tao, Y.; Bao, Z. A.; Leclerc, M. J. Mater. Chem. 2009, 19, 2921
28. Gu, R.; Hameurlaine, A.; Dehaen, W. Synlett 2006, 1535
29. Gu, R.; Hameurlaine, A.; Dehaen, W. J. Org. Chem. 2007, 72, 7207
30. Tholander, J.; Bergman, J. Tetrahedron Lett. 1998, 39, 1619
31. Tholander, J.; Bergman, J. Tetrahedron 1999, 55, 6243
32. Wahlstrom, N.; Stensland, B.; Bergman, J. Synthesis 2004, 1187
33. Saito, K.; Sogou, H.; Suga, T.; Kusama, H.; Iwasawa, N. J. Am. Chem. Soc. 2011, 133, 689
34. Allegretti, P. A.; Ferreira, E. M. Org. Lett. 2011, 13, 5924
35. Allegretti, P. A.; Ferreira, E. M. Chem. Sci 2013, 4, 1053