Palladium-catalyzed carbonation-diketonization of terminal aromatic alkenes via carbon-nitrogen bond cleavage for the synthesis of 1,2-diketones

Journal of Organic Chemistry

Volumn 76, Issue 16, 2011, Pages 6958-6961

  Wang, Azhong ^a   Jiang, Huanfeng ^a   Li, Xianwei ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BOND CLEAVAGES; NITROALKANES; TERMINAL ALKENES;

AROMATIC COMPOUNDS; CATALYSIS; KETONES; PARAFFINS; SYNTHESIS (CHEMICAL);

OLEFINS;

1,2 DIKETONE; ALKENE; AROMATIC HYDROCARBON; CARBON; KETONE DERIVATIVE; NITROALKANE; NITROGEN; OXYGEN; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; ATMOSPHERE; CARBONATION DIKETONIZATION REACTION; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; SYNTHESIS;

EID: 80051712056     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201029p     Document Type: Article

References (29)

1. Guo, S.; Qian, B.; Xie, Y.; Xia, C.; Huang, H. Org. Lett. 2011, 13, 522
2. Kuninobu, Y.; Nishi, M.; Takai, K. Chem. Commun. 2010, 46, 8860
3. Kok, G. B.; Pye, C. C.; Singer, R. D.; Scammells, P. J. J. Org. Chem. 2010, 75, 4806
4. Sabiah, S.; Lee, C.-S.; Hwang, W.-S.; Lin, I. J. B. Organometallics 2010, 29, 290
5. Liu, C.-R.; Li, M.-B.; Cheng, D.-J.; Yang, C.-F.; Tian, S.-K. Org. Lett. 2009, 11, 2543
6. Hollmann, D.; Bähn, S.; Tillack, A.; Beller, M. Angew. Chem., Int. Ed. 2007, 46, 8291
7. Nechab, M.; Kumar, D. N.; Philouze, C.; Einhorn, C.; Einhorn, J. Angew. Chem., Int. Ed. 2007, 46, 3080
8. Zacuto, M. J.; Xu, F. J. Org. Chem. 2007, 72, 6298
9. Liu, C.-R.; Yang, F.-L.; Jin, Y. Z.; Ma, X.-T.; Cheng, D.-J.; Li, N.; Tian, S.-K. Org. Lett. 2010, 12, 3832
10. Anbarasan, P.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2011, 50, 519
11. Jiang, T. S.; Li, J. H. Chem. Commun. 2009, 7236
12. Ueno, S.; Chatani, N.; Kakiuchi, F. J. Am. Chem. Soc. 2007, 129, 6098
13. Liu, Z.; Larock, R. C. J. Am. Chem. Soc. 2005, 127, 13112
14. Golisz, S. R.; Hazari, N.; Labinger, J. A.; Bercaw, J. E. J. Org. Chem. 2009, 74, 8441
15. Ozkay, Y.; Işikdaǧ, I.; Incesu, Z.; Akalin, G. Eur. J. Med. Chem. 2010, 45, 3320
16. Deng, X.; Mani, N. S. Org. Lett. 2006, 8, 269
17. Wadkins, R. M.; Hyatt, J. L.; Wei, X.; Yoon, K. J. P.; Wierdl, M.; Edwards, C. C.; Morton, C. L.; Obenauer, J. C.; Damodaran, K.; Beroza, P.; Danks, M. K.; Potter, P. M. J. Med. Chem. 2005, 48, 2906
18. Wolkenberg, S. E.; Wisnoski, D. D.; Leister, W. H.; Wang, Y.; Zhao, Z.; Lindsley, C. W. Org. Lett. 2004, 6, 1453
19. Zhang, C.; Jiao, N. J. Am. Chem. Soc. 2010, 132, 28
20. Ren, W.; Xia, Y.; Ji, S.-J.; Zhang, Y.; Wan, X.; Zhao, J. Org. Lett. 2009, 11, 1841
21. Tanner, D. D.; Harrison, D. J.; Chen, J.; Kharrat, A.; Wayner, D. D. M.; Griller, D.; McPhee, D. J. J. Org. Chem. 1990, 55, 3321
22. Ono, N.; Miyake, H.; Kamimura, A.; Hamamoto, I.; Tamura, R.; Kaji, A. Tetrahedron 1985, 41, 4013
23. Ono, N.; Miyake, H.; Tamura, R.; Kaji, A. Tetrahedron Lett. 1981, 22, 1705
24. Tanner, D. D.; Blackburn, E. V.; Diaz, G. E. J. Am. Chem. Soc. 1981, 103, 1557
25. Nakayama, H.; Itoh, A. Tetrahedron Lett. 2007, 48, 1131
26. Miyamoto, S.; Martinez, G. R.; Medeiros, M. H. G.; Mascio, P. D. J. Am. Chem. Soc. 2003, 125, 6172
27. Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981.
28. Lee, J. C.; Park, H.-J.; Park, J. Y. Tetrahedron Lett. 2002, 43, 5661
29. Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573