Palladium-catalyzed alkenylation via sp2 C-H bond activation using phenolic hydroxyl as the directing group

Journal of Organic Chemistry

Volumn 79, Issue 7, 2014, Pages 3200-3205

  Zhang, Chun ^a   Ji, Jing ^a   Sun, Peipei ^a  

^a NANJING NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; FUNCTIONAL GROUPS;

BENZOQUINONES; CH-BOND ACTIVATION; DIRECTING GROUPS; PALLADIUM-CATALYZED; PHENOL DERIVATIVES; PHENOLIC HYDROXYL; PHENOLIC HYDROXYL GROUP; REGIOSELECTIVE SYNTHESIS;

ALKENYLATION;

ALKENE DERIVATIVE; BENZOQUINONE DERIVATIVE; CARBON; HYDROGEN; OXIDIZING AGENT; PALLADIUM; PHENOL DERIVATIVE; ALKENE;

ARTICLE; ATMOSPHERE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL BOND; COLUMN CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; CATALYSIS; CHEMISTRY; HYDROGEN BOND; STEREOISOMERISM;

ALKENES; BENZOQUINONES; CATALYSIS; HYDROGEN BONDING; PALLADIUM; PHENOLS; STEREOISOMERISM;

EID: 84898070982     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4028825     Document Type: Article

References (41)

1. Daugulis, O.; Do, H. Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074
2. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
3. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
4. Sun, C. L.; Li, B. J.; Shi, Z. J. Chem. Commun. 2010, 46, 677
5. Daugulis, O. Top. Curr. Chem. 2010, 292, 57-84
6. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
7. Sun, C. L.; Li, B. J.; Shi, Z. J. Chem. Rev. 2011, 111, 1293
8. Liu, C.; Zhang, H.; Shi, W.; Lei, A. W. Chem. Rev. 2011, 111, 1780
9. Davies, H. M. L.; Du Bois, J.; Yu, J.-Q. Chem. Soc. Rev. 2011, 40, 1855 and other reviews in this themed issue
10. Li, B. J.; Shi, Z. J. Chem. Soc. Rev. 2012, 41, 5588
11. Neufeldt, S. R.; Sanford, M. S. Acc. Chem. Res. 2012, 45, 936
12. Li, B.; Dixneuf, P. H. Chem. Soc. Rev. 2013, 42, 5744
13. Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788
14. Giri, R.; Maugel, N.; Li, J.-J.; Wang, D.-H.; Breazzano, S. P.; Saunders, L. B.; Yu, J.-Q. J. Am. Chem. Soc. 2007, 129, 3510
15. Giri, R.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 14082
16. Wang, D.-H.; Mei, T.-S.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 17676
17. Zhang, Y.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 14654
18. Wang, D.-H.; Engle, K. M.; Shi, B.-F.; Yu, J.-Q. Science 2010, 327, 315
19. Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2010, 49, 6169
20. Gandeepan, P.; Parthasarathy, K.; Cheng, C. H. J. Am. Chem. Soc. 2010, 132, 8569
21. Patureau, F. W.; Besset, T.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 1064
22. Leow, D.; Li, G.; Mei, T.-S.; Yu, J.-Q. Nature 2012, 486, 518
23. Li, W.; Xu, Z. P.; Sun, P. P.; Jiang, X. Q.; Fang, M. Org. Lett. 2011, 13, 1286
24. Li, W.; Sun, P. P. J. Org. Chem. 2012, 77, 8362
25. Du, B. N.; Jiang, X. Q.; Sun, P. P. J. Org. Chem. 2013, 78, 2786
26. Lu, Y.; Leow, D.; Wang, X. S.; Engle, K. M.; Yu, J.-Q. Chem. Sci. 2011, 2, 967
27. Luo, S.; Luo, F. X.; Zhang, X. S.; Shi, Z. J. Angew. Chem., Int. Ed. 2013, 52, 10598
28. Lee, T. H.; Jayakumar, J.; Cheng, C. H.; Chuang, S. C. Chem. Commun. 2013, 49, 11797
29. Inamoto, K.; Kadokawa, J.; Kondo, Y. Org. Lett. 2013, 15, 3962
30. Wang, X. S.; Lu, Y.; Dai, H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 12203
31. Xiao, B.; Gong, T. J.; Liu, Z. J.; Liu, J. H.; Luo, D. F.; Xu, J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 9250
32. Wei, Y.; Yoshikai, N. Org. Lett. 2011, 13, 5504
33. Zhao, J. J.; Wang, Y.; He, Y. M.; Liu, L. Y.; Zhu, Q. Org. Lett. 2012, 14, 1078
34. Thirunavukkarasu, V. S.; Donati, M.; Ackermann, L. Org. Lett. 2012, 14, 3416
35. Miura, M.; Tsuda, T.; Satoh, T.; Nomura, M. Chem. Lett. 1997, 1103
36. Dorta, R.; Togni, A. Chem. Commun. 2003, 760
37. Bedford, R. B.; Coles, S. J.; Hursthouse, M. B.; Limmert, M. E. Angew. Chem., Int. Ed. 2003, 42, 112
38. Lu, Y.; Wang, D.-H.; Engle, K. H.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 5916
39. Mewald, M.; Schiffner, J. A.; Oestreich, M. Angew. Chem., Int. Ed. 2012, 51, 1763
40. Shi, Z. Z.; Schroder, N.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 8092
41. Bras, J. L.; Muzart, J. Chem. Rev. 2011, 111, 1170