Oxidative C-H functionalization: A novel strategy for the acetoxylation/alkoxylation of arenes tethered to 3,4-dihydroisoquinolines

Tetrahedron Letters

Volumn 53, Issue 45, 2012, Pages 6091-6094

  Subba Reddy, B V ^a   Umadevi, N ^a   Narasimhulu, G ^a   Yadav, J S ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

1 Aryl 3,4 dihydroisoquinolines; Acetoxylation; Alkoxylation; C H activation; Hypervalent iodine reagent

Indexed keywords

1 ARYL 3,4 DIHYDROISOQUINOLINE; CARBON; HYDROGEN; PALLADIUM COMPLEX; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; QUINOLINE DERIVATIVE; SOLIFENACIN; STRESS ACTIVATED PROTEIN KINASE INHIBITOR; UNCLASSIFIED DRUG;

ACETOXYLATION; ALKOXYLATION; ARTICLE; DRUG STRUCTURE; HYDROGEN BOND; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; OXIDATION; REDUCTION; STOICHIOMETRY;

EID: 84867244760     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.08.124     Document Type: Article

References (51)

1. M. Chang, W. Li, and X. Zhang Angew. Chem., Int. Ed. 50 2011 10679
2. K.M. Lee, J.C. Kim, P. Kang, W.K. Lee, H. Eumb, and J.-H. Ha Tetrahedron 68 2012 883
3. J.D. Phillipson, M.F. Roberts, and M.H. Zenk The Chemistry and Biology of Isoquinoline Alkaloids 1985 Springer Berlin
4. D. Jack, and R. Williams Chem. Rev. 102 2002 1669
5. K.W. Bentley Nat. Prod. Rep. 23 2006 444
6. R.K. Tiwari, D. Singh, J. Singh, A.K. Chhillar, R. Chandra, and A.K. Verma Eur. J. Med. Chem. 41 2006 40
7. P. Cheng, N. Huang, Z.Y. Jiang, Q. Zhang, Y.T. Zheng, J.J. Chen, X.M. Zhang, and Y.B. Ma Bioorg. Med. Chem. Lett. 18 2008 2475
8. K.X. Chen, H.Y. Xie, Z.G. Li, and J.R. Gao Bioorg. Med. Chem. Lett. 18 2008 5381
9. R. Gitto, M.L. Barreca, L. De Luca, G. De Sarro, G. Ferreri, S. Quartarone, E. Russo, A. Constanti, and A. Chimirri J. Med. Chem. 46 2003 197
10. R. Naito, Y. Yonetoku, Y. Okamoto, A. Toyoshima, K. Ikeda, and M. Takeuchi J. Med. Chem. 48 2005 6597
11. J.A. Christopher, F.L. Atkinson, B.D. Bax, M.J.B. Brown, A.C. Champigny, T.T. Chuang, E.J. Jones, J.E. Mosley, and J.R. Musgrave Bioorg. Med. Chem. Lett. 19 2009 2230
12. A. Bermejo, I. Andreu, F. Suvire, S. Leonce, D.H. Caignard, P. Renard, A. Pierre, R.D. Enriz, D. Cortes, and N. Cabedo J. Med. Chem. 45 2002 5058
13. E.M. Beccalli, G. Broggini, M. Martinelli, and S. Sottocornola Chem. Rev. 107 2007 5318
14. D. Alberico, M.E. Scott, and M. Lautens Chem. Rev. 107 2007 174
15. R. Giri, N.L. Maugel, J.J. Li, D.H. Wang, S.P. Breazzano, L.B. Saunders, and J.Q. Yu J. Am. Chem. Soc. 129 2007 3510
16. G. Cai, Y. Fu, Y. Li, X. Wan, and Z. Shi J. Am. Chem. Soc. 129 2007 7666
17. Z.J. Shi, B. Li, X. Wan, J. Cheng, Z. Fang, B. Cao, C. Qin, and Y. Wang Angew. Chem., Int. Ed. 46 2007 5554
18. W.-Y. Yu, W.N. Sit, K.-M. Lai, Z. Zhou, and A.S.C. Chan J. Am. Chem. Soc. 130 2008 3304
19. K.L. Hull, and M.S. Sanford J. Am. Chem. Soc. 129 2007 11904
20. J.Q. Yu, R. Giri, and X. Chen Org. Biomol. Chem. 4 2006 4041
21. X. Chen, J.J. Li, X.S. Hao, C.E. Goodhue, and J.Q. Yu J. Am. Chem. Soc. 128 2006 78
22. X. Chen, C.E. Goodhue, and J.Q. Yu J. Am. Chem. Soc. 128 2006 12634
23. V.G. Zaitsev, D. Shabashov, and O. Daugulis J. Am. Chem. Soc. 127 2005 13154
24. O. Daugulis, and V.G. Zaitsev Angew. Chem., Int. Ed. 44 2005 4046
25. K. Orito, A. Horibata, T. Nakamura, H. Ushito, H. Nagasaki, M. Yuguchi, S. Yamashita, and M. Tokuda J. Am. Chem. Soc. 126 2004 14342
26. H. Wakui, S. Kawasaki, T. Satoh, M. Miura, and M. Nomura J. Am. Chem. Soc. 126 2004 8658
27. L.V. Desai, D.T. Ren, and T. Rosner Org. Lett. 12 2010 1032
28. N. Yoshikai, A. Matsumoto, J. Norinder, and E. Nakamura Angew. Chem., Int. Ed. 48 2009 2925
29. X. Zhao, C.S. Yeung, and V.M. Dong J. Am. Chem. Soc. 132 2010 5837
30. S. Gu, C. Chen, and W. Chen J. Org. Chem. 74 2009 7203
31. H.Y. Thu, W.Y. Yu, and C.M. Che J. Am. Chem. Soc. 128 2006 9048
32. X. Wan, Z. Ma, B. Li, K. Zhang, S. Cao, S. Zhang, and Z. Shi J. Am. Chem. Soc. 128 2006 7416
33. W.C.P. Tsang, N. Zheng, and S.L. Buchwald J. Am. Chem. Soc. 127 2005 14560
34. R. Giri, J. Liang, J.G. Lei, J.J. Li, D.H. Wang, X. Chen, I.C. Naggar, C. Guo, B.M. Foxman, and J.Q. Yu Angew. Chem., Int. Ed. 44 2005 7420
35. M. Wasa, B.T. Worrell, and J.-Q. Yu Angew. Chem., Int. Ed. 49 2010 1275
36. N. Chernyak, A.S. Dudnik, C. Huang, and V.J. Gevorgyan J. Am. Chem. Soc. 132 2010 8270
37. C. Huang, B. Chattopadhyay, and V.J. Gevorgyan J. Am. Chem. Soc. 133 2011 12406
38. C. Wang, H. Chen, Z. Wang, J. Chen, and Y. Huang Angew. Chem., Int. Ed. 51 2012 7242
39. J.M. Racowski, A.R. Dick, and M.S. Sanford J. Am. Chem. Soc. 131 2009 10974
40. A.R. Dick, K.L. Hull, and M.S. Sanford J. Am. Chem. Soc. 126 2004 2300
41. G.-W. Wang, T.-T. Yuan, and X.-L. Wu J. Org. Chem. 73 2008 4717
42. G.-W. Wang, and T.-T. Yuan J. Org. Chem. 75 2010 476
43. K.J. Stowers, and M.S. Sanford Org. Lett. 11 2009 4584
44. L.V. Desai, H.A. Malik, and M.S. Sanford Org. Lett. 8 2006 1141
45. D. Kalyani, and M.S. Sanford Org. Lett. 7 2005 4149
46. B.V.S. Reddy, L.R. Reddy, and E.J. Corey Org. Lett. 8 2006 3391
47. B.V.S. Reddy, K. Ramesh, and J.S. Yadav Synlett 2011 169
48. B.V.S. Reddy, G. Revathi, A.S. Reddy, and J.S. Yadav Synlett 2011 2374
49. B.V.S. Reddy, G. Revathi, A.S. Reddy, and J.S. Yadav Tetrahedron Lett. 52 2011 5926
50. B.V.S. Reddy, G. Narasimhulu, N. Umadevi, and J.S. Yadav Synlett 2012 1364
51. C.H. Yang, C.C. Tai, and I.W. Sun J. Mater. Chem. 14 2004 947