Double C-H activation: The palladium-catalyzed direct C-arylation of xanthines with arenes

Organic Letters

Volumn 13, Issue 6, 2011, Pages 1378-1381

  Malakar, Chandi C ^a   Schmidt, Dietmar ^a   Conrad, Jürgen ^a   Beifuss, Uwe ^a  

^a UNIVERSITY OF HOHENHEIM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

OXYGEN; PALLADIUM; XANTHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; OXYGEN; PALLADIUM; XANTHINES;

EID: 79952590882     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200065s     Document Type: Article

References (29)

1. de Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, Germany, 2004.
2. Reviews: Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792-9826
3. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174-238
4. Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400-3420
5. Åkermark, B.; Eberson, L.; Jonsson, E.; Pettersson, E. J. Org. Chem. 1975, 40, 1365-1367
6. Gruner, K. K.; Knölker, H.-J. Org. Biomol. Chem. 2008, 6, 3902-3904
7. Liegault, B.; Lee, D.; Huestis, M. P.; Stuart, D. R.; Fagnou, K. J. Org. Chem. 2008, 73, 5022-5028
8. Watanabe, T.; Ueda, S.; Inuki, S.; Oishi, S.; Fujii, N.; Ohno, H. Chem. Commun 2007, 4516-4518
9. Lessene, G.; Feldman, K. S. Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, Germany, 2002; p 479.
10. Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172-1175
11. Stuart, D. R.; Villemure, E.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 12072-12073
12. Dwight, T. A.; Rue, N. R.; Charyk, D.; Josselyn, R.; DeBoef, B. Org. Lett. 2007, 9, 3137-3139
13. Potavathri, S.; Dumas, A. S.; Dwight, T. A.; Naumiec, G. R.; Hammann, J. M.; DeBoef, B. Tetrahedron Lett. 2008, 49, 4050-4053
14. Potavathri, S.; Pereira, K. C.; Gorelsky, S. I.; Pike, A.; LeBris, A. P.; DeBoef, B. J. Am. Chem. Soc. 2010, 132, 14676-14681
15. Cho, S. H.; Hwang, S. J.; Chang, S. J. Am. Chem. Soc. 2008, 130, 9254-9256
16. Brasche, G.; Garcia-Fortanet, J.; Buchwald, S. L. Org. Lett. 2008, 10, 2207-2210
17. Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 11904-11905
18. Li, B.-J.; Tian, S.-L.; Fang, Z.; Shi, Z.-J. Angew. Chem., Int. Ed. 2008, 47, 1115-1118
19. Wei, Y.; Su, W. J. Am. Chem. Soc. 2010, 132, 16377-16379
20. He, C.-Y.; Fan, S.; Zhang, X. J. Am. Chem. Soc. 2010, 132, 12850-12852
21. Hayallah, A. M.; Sandoval-Ramírez, J.; Reith, U.; Schobert, U.; Preiss, B.; Schumacher, B.; Daly, J. W.; Müller, C. E. J. Med. Chem. 2002, 45, 1500-1510
22. Yan, L.; Müller, C. E. J. Med. Chem. 2004, 47, 1031-1043
23. Kalla, R. V.; Elzein, E.; Perry, T.; Li, X.; Palle, V.; Varkhedkar, V.; Gimbel, A.; Maa, T.; Zeng, D.; Zablocki, J. J. Med. Chem. 2006, 49, 3682-3692
24. Chiong, H. A.; Daugulis, O. Org. Lett. 2007, 9, 1449-1451
25. Zhao, D.; Wang, W.; Yang, F.; Lan, J.; Yang, L.; Gao, G.; You, J. Angew. Chem., Int. Ed. 2009, 48, 3296-3300
26. Zhao, D.; Wang, W.; Lian, S.; Yang, F.; Lan, J.; You, J. Chem.-Eur. J. 2009, 15, 1337-1340
27. Ackermann, L.; Althammer, A.; Fenner, S. Angew. Chem., Int. Ed. 2009, 48, 201-204
28. Liu, B.; Qin, X.; Li, K.; Li, X.; Guo, Q.; Lan, J.; You, J. Chem.-Eur. J. 2010, 16, 11836-11839
29. Xi, P.; Yang, F.; Qin, S.; Zhao, D.; Lan, J.; Gao, G.; Hu, C.; You, J. J. Am. Chem. Soc. 2010, 132, 1822-1824