Pd-catalyzed multiple C-H functionalization to construct biologically active compounds from aryl aldoxime ethers with arenes

Chemistry - A European Journal

Volumn 17, Issue 52, 2011, Pages 14723-14726

  Thirunavukkarasu, Vedhagiri S ^a   Cheng, Chien Hong ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

C H activation; cyclization; fluorenone; oxime ether; palladium

Indexed keywords

ALDOXIMES; BIOLOGICALLY ACTIVE COMPOUNDS; C-H ACTIVATION; C-H FUNCTIONALIZATION; CH-BOND ACTIVATION; FLUORENONES; OXIDATIVE CYCLIZATION; OXIME ETHERS; PALLADIUM COMPLEXES;

ACTIVATION ANALYSIS; AROMATIC COMPOUNDS; BIOACTIVITY; CATALYSIS; ETHERS; KETONES; PALLADIUM; PALLADIUM COMPOUNDS;

CYCLIZATION;

ETHER DERIVATIVE; FLUORENE DERIVATIVE; OXIME; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; HYDROGEN BOND;

CATALYSIS; CYCLIZATION; ETHERS; FLUORENES; HYDROGEN BONDING; MOLECULAR STRUCTURE; OXIMES; PALLADIUM;

EID: 83755163234     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102996     Document Type: Article

References (60)

1. R. K. Arafa, T. Wenzler, F. A. Taniou, W. D. Stephens, C. E. Wilson, D. W. Boykin, J. Med. Chem. 2005, 48, 5480
2. W. Zeng, T. E. Ballard, A. G. Tkachenko, V. A. Burns, D. L. Feldheim, C. Melander, Bioorg. Med. Chem. Lett. 2006, 16, 5148.
3. E. González-Cantalapiedra, Ó. de Frutos, C. Atienza, C. Mateo, A. M. Echavarren, Eur. J. Org. Chem. 2006, 1430
4. J.-M. Fu, B.-P. Zhao, M. J. Sharp, V. Snieckus, Can. J. Chem. 1994, 72, 227
5. W. Wang, V. Snieckus, J. Org. Chem. 1992, 57, 424
6. M. V. Sargent, J. Chem. Soc. Perkin Trans. 1 1987, 2553.
7. H. Usta, A. Facchetti, J. T. Marks, Org. Lett. 2008, 10, 1385
8. K. Itami, K. Tonogaki, T. Nokami, Y. Ohashi, J.-I. Yoshida, Angew. Chem. 2006, 118, 2464
9. Angew. Chem. Int. Ed. 2006, 45, 2404
10. D. A. Shultz, J. C. Sloop, G. Washington, J. Org. Chem. 2006, 71, 9104
11. F. Cariati, U. Caruso, R. Centore, A. De Maria, M. Fusco, B. Panunzi, A. Roviello, A. Tuzi, Opt. Mater. 2004, 27, 91.
12. I.-J. Kang, L.-W. Wang, S.-J. Hsu, C.-C. Lee, Y.-C. Lee, Y.-S. Wu, A. Yueh, J.-C. Wang, T.-A. Hsu, Y.-S. Chao, J.-H. Chern, Bioorg. Med. Chem. Lett. 2009, 19, 6063.
13. W. Qian, E. Jin, W. Bao, Y. Zhang, Angew. Chem. 2005, 117, 974
14. Angew. Chem. Int. Ed. 2005, 44, 952
15. A. Dhakshinamoorthy, M. Alvaro, H. Garcia, J. Catal. 2009, 267, 1
16. S. Reim, M. Lau, P. Langer, Tetrahedron Lett. 2006, 47, 6903
17. J. N. Moorthy, S. Samanta, J. Org. Chem. 2007, 72, 9786
18. G. Qabaja, G. B. Jones, J. Org. Chem. 2000, 65, 7187
19. M. A. Campo, R. C. Larock, Org. Lett. 2000, 2, 3675
20. N. Chatani, A. Kamitani, M. Oshita, Y. Fukumoto, S. Murai, J. Am. Chem. Soc. 2001, 123, 12686.
21. J. Zhao, D. Yue, M. A. Campo, R. C. Larock, J. Am. Chem. Soc. 2007, 129, 5288.
22. D. Shabashov, J. R. M. Maldonado, O. Daugulis, J. Org. Chem. 2008, 73, 7818.
23. V. S. Thirunavukkarasu, K. Parthasarathy, C.-H. Cheng, Angew. Chem. 2008, 120, 9604
24. Angew. Chem. Int. Ed. 2008, 47, 9462.
25. C.-L. Sun, N. Liu, B.-J. Li, D.-G. Yu, Y. Wang, Z.-J. Shi, Org. Lett. 2010, 12, 184.
26. L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. 2009, 121, 6161
27. Angew. Chem. Int. Ed. 2009, 48, 9792
28. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
29. X. Chen, K. M. Engle, D. H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196
30. Angew. Chem. Int. Ed. 2009, 48, 5094
31. D. R. Stuart, K. Fagnou, Science 2007, 316, 1172
32. T. A. Dwight, N. R. Rue, D. Charyk, R. Josselyn, B. DeBoef, Org. Lett. 2007, 9, 3137
33. P. Xi, F. Yang, S. Qin, D. Zhao, J. Lan, G. Gao, C. Hu, J. You, J. Am. Chem. Soc. 2010, 132, 1822
34. Y. Wei, W. Su, J. Am. Chem. Soc. 2010, 132, 16377.
35. G. Brasche, J. García-Fortanet, S. L. Buchwald, Org. Lett. 2008, 10, 2207
36. B.-J. Li, S.-L. Tian, Z. Fang, Z.-J. Shi, Angew. Chem. 2008, 120, 1131
37. Angew. Chem. Int. Ed. 2008, 47, 1115
38. K. L. Hull, M. S. Sanford, J. Am. Chem. Soc. 2007, 129, 11904
39. K. L. Hull, M. S. Sanford, J. Am. Chem. Soc. 2009, 131, 9651
40. S. H. Cho, S. J. Hwang, S. Chang, J. Am. Chem. Soc. 2008, 130, 9254
41. X. Zhao, C. S. Yeung, V.M. Dong, J. Am. Chem. Soc. 2010, 132, 5837
42. C. S. Yeung, X. Zhao, N. Borduas, V. M. Dong, Chem. Sci. 2010, 1, 331
43. M. J. Tredwell, M. Gulias, N. G. Bremeyer, C. C. C. Johansson, B. S. L. Collins, M. J. Gaunt, Angew. Chem. Int. Ed. 2011, 50, 1076
44. S. J. Hwang, H. J. Kim, S. Chang, Org. Lett. 2009, 11, 4588
45. C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Commun. 2010, 46, 677.
46. V. S. Thirunavukkarasu, K. Parthasarathy, C.-H. Cheng, Chem. Eur. J. 2010, 16, 1436
47. P. Gandeepan, K. Parthasarathy, C.-H. Cheng, J. Am. Chem. Soc. 2010, 132, 8569
48. K. Muralirajan, K. Parthasarathy, C.-H. Cheng, Angew. Chem. 2011, 123, 4255
49. Angew. Chem. Int. Ed. 2011, 50, 4169
50. T. T. Jayanth, C.-H. Cheng, Chem. Commun. 2006, 894
51. P. Shukla, C.-H. Cheng, Org. Lett. 2006, 8, 2867
52. K. Parthasarathy, M. Jeganmohan, C.-H. Cheng, Org. Lett. 2008, 10, 325.
53. L. V. Desai, H. A. Malik, M. S. Sanford, Org. Lett. 2006, 8, 1141
54. G.-W. Wang, T.-T. Yuan, X.-L. Wu, J. Org. Chem. 2008, 73, 4717
55. K. L. Hull, E. L. Lanni, M. S. Sanford, J. Am. Chem. Soc. 2006, 128, 14047
56. C. F. Rosewall, P. A. Sibbald, D. V. Liskin, F. E. Michael, J. Am. Chem. Soc. 2009, 131, 9488
57. P. A. Sibbald, C. F. Rosewall, R. D. Swartz, F. E. Michael, J. Am. Chem. Soc. 2009, 131, 15945
58. J. Karthikeyan, C.-H. Cheng, Angew. Chem. 2011, 123, 10054
59. Angew. Chem. Int. Ed. 2011, 50, 9880
60. L.-M. Xu, B.-J. Li, Z. Yang, Z.-J. Shi, Chem. Soc. Rev. 2010, 39, 712.