Synthesis of phenanthrone derivatives from sec- alkyl aryl ketones and aryl halides via a palladium-catalyzed dual C-H bond activation and enolate cyclization

Journal of the American Chemical Society

Volumn 132, Issue 25, 2010, Pages 8569-8571

  Gandeepan, Parthasarathy ^a   Parthasarathy, Kanniyappan ^a   Cheng, Chien Hong ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL HALIDES; ARYL IODIDES; ARYL KETONES; C-H ACTIVATION; CATALYTIC REACTIONS; CH-BOND ACTIVATION; ENOLATES; REACTION MECHANISM;

ACTIVATION ANALYSIS; ALKYLATION; CATALYSIS; HYDROCARBONS; KETONES; PALLADIUM; SYNTHESIS (CHEMICAL);

CYCLIZATION;

3 CHLOROACETOPHENONE; 4 METHOXYIODOBENZENE; ACETOPHENONE; ALKYL ARYL KETONE; ANION; CARBON; ENOLATE; HALIDE; IODIDE; IODOBENZENE; PALLADIUM; PHENANTHRONE DERIVATIVE; SILVER; SODIUM CHLORIDE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; HYDROGEN BOND; SYNTHESIS;

EID: 77953892735     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1026248     Document Type: Article

References (28)

1. Dick, A. R. and Sanford, M. S. Tetrahedron 2006, 62, 2439
2. Stuart, D. R. and Fagnou, K. Science 2007, 316, 1172
3. Alberico, D., Scott, M. E., and Lautens, M. Chem. Rev. 2007, 107, 174
4. Chen, X., Engle, K. M., Wang, D.-H., and Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
5. Daugulis, O., Do, H.-Q., and Shabashov, D. Acc. Chem. Res. 2009, 42, 1074
6. Ackermann, L., Vicente, R., and Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792
7. Lyons, T. W. and Sanford, M. S. Chem. Rev. 2010, 110, 1147
8. Jun, C.-H., Moon, C. W., and Lee, D.-Y. Chem.-Eur. J. 2002, 8, 2422
9. Park, Y. J. and Jun, C.-H. Bull. Korean Chem. Soc. 2005, 26, 877
10. Colby, D. A., Bergman, R. G., and Ellman, J. A. Chem. Rev. 2010, 110, 624
11. Kakiuchi, F., Uetsuhara, T., Tanaka, Y., Chatani, N., and Murai, S. J. Mol. Catal. A: Chem. 2002, 182-183, 511
12. Kakiuchi, F., Yamamoto, Y., Chatani, N., and Murai, S. Chem. Lett. 1995, 24, 681
13. Tsuchikama, K., Kasagawa, M., Hashimoto, Y.-K., Endo, K., and Shibata, T. J. Organomet. Chem. 2008, 693, 3939
14. Murai, S., Kakiuchi, F., Sekine, S., Tanaka, Y., Kamatani, A., Sonoda, M., and Chatani, N. Nature 1993, 366, 529
15. Sato, T., Kakiuchi, F., Chatani, N., and Murai, S. Chem. Lett. 1998, 27, 893
16. Martinez, R., Chevalier, R., Darses, S., and Genet, J. P. Angew. Chem., Int. Ed. 2006, 45, 8232
17. Martinez, R., Simon, M.-O., Chevalier, R., Genet, J. P., and Darses, S. J. Am. Chem. Soc. 2009, 131, 7887
18. Ishii, Y., Chatani, N., Kakiuchi, F., and Murai, S. Tetrahedron Lett. 1997, 38, 7565
19. Terao, Y., Kametani, Y., Wakui, H., Satoh, T., Miura, M., and Namura, M. Tetrahedron 2001, 57, 5967
20. Kakiuchi, F., Kan, S., Igi, K., Chatani, N., and Murai, S. J. Am. Chem. Soc. 2003, 125, 1698
21. Parthasarathy, K., Jeganmohan, M., and Cheng, C.-H. Org. Lett. 2008, 8, 325
22. Parthasarathy, K. and Cheng, C.-H. J. Org. Chem. 2009, 74, 9359
23. Thirunavukkarasu, V. S., Parthasarathy, K., and Cheng, C.-H. Angew. Chem., Int. Ed. 2008, 47, 9462
24. Thirunavukkarasu, V. S., Parthasarathy, K., and Cheng, C.-H. Chem.-Eur. J. 2010, 16, 1436
25. Lebrasseur, N. and Larrosa, I. J. Am. Chem. Soc. 2008, 130, 2926
26. Cho, S. H., Hwang, S. J., and Chang, S. J. Am. Chem. Soc. 2008, 130, 9254
27. Chen, X., Goodhue, C. E., and Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 12634
28. Faccini, F., Motti, E., and Catellani, M. J. Am. Chem. Soc. 2004, 126, 78