Ligand-enabled methylene C(sp3)-H bond activation with a Pd(II) catalyst

Journal of the American Chemical Society

Volumn 134, Issue 45, 2012, Pages 18570-18572

  Wasa, Masayuki ^a   Chan, Kelvin S L ^a   Zhang, Xing Guo ^a   He, Jian ^a   Miura, Masanori ^a   Yu, Jin Quan ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL GROUP; CYCLIC AMIDES; ELECTRON-RICH; H-BONDS;

AMIDES; PALLADIUM COMPOUNDS;

LIGANDS;

CARBENE; PALLADIUM COMPLEX; QUINOLONE;

ARTICLE; ARYLATION; CATALYST; CHEMICAL STRUCTURE; CONTROLLED STUDY; ELECTRON; HYDROGEN BOND; LIGAND BINDING;

AMIDES; CATALYSIS; HYDROGEN BONDING; LIGANDS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PYRIDINES; QUINOLINES;

EID: 84869456845     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja309325e     Document Type: Article

References (38)

1. Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074
2. Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem. - Eur. J. 2010, 16, 2654
3. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
4. Wasa, M.; Engle, K. M.; Yu, J.-Q. Isr. J. Chem. 2010, 50, 605
5. Baudoin, O. Chem. Soc. Rev. 2011, 40, 4902
6. Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417
7. Doyle, M. P. J. Org. Chem. 2006, 71, 9253
8. Du Bois, J.; Zalatan, D. N. J. Am. Chem. Soc. 2008, 130, 9220
9. Milczek, E.; Boudet, N.; Blakey, S. Angew. Chem., Int. Ed. 2008, 47, 6825
10. Wasa, M.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 9886
11. Wasa, M.; Yu, J-.Q. Tetrahedron 2010, 66, 4811
12. Wasa, M.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3680
13. Yoo, E. J.; Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 17378
14. Wasa, M.; Engle, K. M.; Lin, D. W.; Yoo, E. J.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 19598
15. Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Shaw, B. L.; Weeks, B. J. Chem. Soc., Dalton Trans. 1979, 1972
16. Hiraki, K.; Fuchita, Y.; Matsumoto, Y. Chem. Lett. 1984, 1947
17. Canty, A. J.; Patel, J.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 2000, 607, 194
18. Sjovall, S.; Wendt, O. F.; Andersson, C. J. Chem. Soc., Dalton Trans. 2002, 1396
19. Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154
20. Reddy, L. R.; Reddy, B. V. S.; Corey, E. J. Org. Lett. 2006, 8, 2819
21. Chen, X.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 12634
22. Giri, R.; Maugel, N.; Foxman, B. M.; Yu, J.-Q. Organometallics 2008, 27, 1667
23. Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2010, 132, 3965
24. Feng, Y. Q.; Wang, Y. J.; Landgraf, B.; Liu, S.; Chen, G. Org. Lett. 2010, 12, 3414
25. He, G.; Chen, G. Angew. Chem., Int. Ed. 2011, 50, 5192
26. Ano, Y.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 12984
27. Gutekunst, W. R.; Baran, P. S. J. Am. Chem. Soc. 2011, 133, 19076
28. Gutekunst, W. R.; Gianatassio, R.; Baran, P. S. Angew. Chem., Int. Ed. 2012, 51, 7507
29. 3)-H bond in trans -decalone O -methyl oxime: Desai, L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542
30. Watanabe, T.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2008, 10, 1759
31. Nakanishi, M.; Katayev, D.; Besnard, C.; Kündig, E. P. Angew. Chem., Int. Ed. 2011, 50, 7438
32. Anas, S.; Cordi, A.; Kagan, H. B. Chem. Commun. 2011, 47, 11483
33. Wang, D. H.; Engle, K. M.; Shi, B. F.; Yu, J.-Q. Science 2010, 327, 315
34. Huang, C.; Chattopadhyay, B.; Gevorgyan, V. J. Am. Chem. Soc. 2011, 133, 12406
35. Novák, P.; Correa, A.; Gallardo-Donaire, J.; Martin, R. Angew. Chem., Int. Ed. 2011, 50, 12236
36. Zhang, Y. H.; Shi, B. F.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 5072
37. Yanagisawa, S.; Ueda, K.; Sekizawa, H.; Itami, K. J. Am. Chem. Soc. 2009, 131, 14622
38. Kubota, A.; Emmert, M. H.; Sanford, M. S. Org. Lett. 2012, 14, 1760