'Ligand-free' palladium-catalyzed direct C-H bond oxidative acyloxylation of 2-arylpyridines with aromatic carboxylic acids

Tetrahedron Letters

Volumn 53, Issue 19, 2012, Pages 2465-2468

  Hu, Chao Jun ^a   Zhang, Xiao Hong ^a   Ding, Qiu Ping ^a,b   Lv, Ting ^a   Ge, Shao Peng ^a   Zhong, Ping ^a  

^a WENZHOU UNIVERSITY   (China)

^b JIANGXI NORMAL UNIVERSITY   (China)

Author keywords

'Ligand free'; 2 Arylpyridines; Acyloxylation; Palladium catalyzed

Indexed keywords

AROMATIC CARBOXYLIC ACID; LIGAND; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIDINE DERIVATIVE;

ACYLOXYLATION; ARTICLE; CATALYSIS; CATALYST; HYDROGEN BOND; LOW TEMPERATURE; OXIDATION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 84862823488     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.03.022     Document Type: Article

References (46)

1. For selected reports on the construction of C-C via direct functionalization of C-H, see: H. Komai, T. Yoshino, S. Matsunaga, and M. Kanai Org. Lett. 13 2011 1706
2. G. Brasche, J. Garcia-Fortanet, and S.L. Buchwald Org. Lett. 10 2008 2207
3. J.C. Lewis, S.H. Wiedemann, R.G. Bergman, and J.A. Ellman Org. Lett. 6 2004 35
4. B. Sezen, and D. Sames Org. Lett. 5 2003 3607
5. D. Saha, L. Adak, and B.C. Ranu Tetrahedron Lett. 51 2010 5624
6. A.S. Tsai, M.E. Tauchert, R.G. Bergman, and J.A. Ellman J. Am. Chem. Soc. 133 2011 1248
7. For selected reports on the construction of C-N via direct functionalization of C-H, see: E.M. Beccalli, G. Broggini, A. Fasana, and M. Rigamonti J. Organomet. Chem. 696 2011 277
8. W.C.P. Tsang, N. Zheng, and S.L. Buchwald J. Am. Chem. Soc. 127 2005 14560
9. M.M. Guru, M.A. Ali, and T. Punniyamurthy Org. Lett. 13 2011 1194
10. W.C.P. Tsang, R.H. Munday, G. Brasche, N. Zheng, and S.L. Buchwald J. Org. Chem. 73 2008 7603
11. S.M. Guo, Y.J. Xie, C.G. Xia, and H.H. Huang Org. Lett. 13 2011 522
12. D. Monguchi, T. Fujiwara, H. Furukawa, and A. Mori Org. Lett. 11 2009 1607
13. For selected reports on the construction of C-O via direct functionalization of C-H, see: K. Chen, J.M. Richter, and P.S. Baran J. Am. Chem. Soc. 130 2008 7247
14. E.W. Kalber, S.R. Whitfield, and M.S. Sanford J. Mol. Catal. A: Chem. 251 2006 108
15. S. Ueda, and H. Nagasawa J. Org. Chem. 74 2009 4272
16. For selected reports on the construction of C-S via direct functionalization of C-H, see: K. Inamoto, C. Hasegawa, K. Hiroya, and T. Doi Org. Lett. 10 2008 5147
17. R.S. Xu, J.P. Wan, H. Mao, and Y.J. Pan J. Am. Chem. Soc. 132 2010 15531
18. S. Fukuzawa, E. Shimizu, Y. Atsuumi, M. Haga, and K. Ogata Tetrahedron Lett. 50 2009 2374
19. D.J.C. Prasad, A.B. Naidu, and G. Sekar Tetrahedron Lett. 50 2009 1411
20. E.A. Jaseer, D.J.C. Prasad, A. Dandapat, and G. Sekar Tetrahedron Lett. 51 2010 5009
21. X.L. Fang, R.Y. Tang, P. Zhong, and J.H. Li Synthesis 24 2009 4183
22. A. Pezzella, A. Palma, A. Iadonisi, A. Napolitano, and M. d'Ischia Tetrahedron Lett. 48 2007 3883
23. L.V. Desai, K.J. Stowers, and M.S. Sanford J. Am. Chem. Soc. 130 2008 13285
24. A.R. Dick, K.L. Hull, and M.S. Sanford J. Am. Chem. Soc. 126 2004 2300
25. A.R. Dick, J.W. Kampf, and M.S. Sanford Organometallics 24 2005 482
26. K.J. Stowers, and M.S. Sanford Org. Lett. 11 2009 4584
27. A.R. Dick, M.S. Remy, J.W. Kampf, and M.S. Sanford Organometallics 26 2007 1365
28. D. Kalyani, and M.S. Sanford Org. Lett. 7 2005 4149
29. P.Y. Choy, C.P. Lau, and F.Y. Kwong J. Org. Chem. 76 2011 80
30. I. Mutule, E. Suna, K. Olofsson, and B. Pelcman J. Org. Chem. 74 2009 7195
31. S.J. Gu, C. Chen, and W.Z. Chen J. Org. Chem. 74 2009 7203
32. G.W. Wang, T.T. Yuan, and X.L. Wu J. Org. Chem. 73 2008 4717
33. Z.J. Liang, J.L. Zhao, and Y.H. Zhang J. Org. Chem. 75 2010 170
34. D.C. Powers, M.A.L. Geibel, J.E.M.N. Klein, and T. Ritter J. Am. Chem. Soc. 131 2009 17050
35. D.C. Powers, D.Y. Xiao, M.A.L. Geibel, and T. Ritter J. Am. Chem. Soc. 132 2010 14530
36. X. Chen, X.S. Hao, C.E. Goodhue, and J.Q. Yu J. Am. Chem. Soc. 128 2006 6790
37. D.H. Wang, X.S. Hao, D.F. Wu, and J.Q. Yu Org. Lett. 8 2006 3387
38. Z.S. Ye, W.H. Wang, F. Luo, S.H. Zhang, and J. Cheng Org. Lett. 11 2009 3974
39. W.H. Wang, F. Luo, S.H. Zhang, and J. Cheng J. Org. Chem. 75 2010 2415
40. W.H. Wang, C.D. Pan, F. Chen, and J. Cheng Chem. Commun. 47 2011 3978
41. C.L. Sun, J. Liu, Y. Wang, X. Zhou, B.J. Li, and Z.J. Shi Synlett 2011 0883
42. X. Chen, C.E. Goodhue, and J.Q. Yu J. Am. Chem. Soc. 128 2006 12634
43. W.Y. Yu, W.N. Sit, Z.Y. Zhou, and A.S.-C. Chan Org. Lett. 11 2009 3174
44. W. Li, Z.W. Yin, X.Q. Jiang, and P.P. Sun J. Org. Chem. 76 2011 8543
45. C.C. Malakar, D. Schmidt, J. Conrad, and U. Beifuss Org. Lett. 13 2011 1378
46. D. Kim, and S. Hong Org. Lett. 13 2011 4466