tert-Butyl peroxybenzoate (TBPB)-mediated 2-isocyanobiaryl insertion with 1,4-dioxane: efficient synthesis of 6-alkyl phenanthridines via C(sp3)-H/C(sp2)-H bond functionalization

Chemical Communications

Volumn 50, Issue 49, 2014, Pages 6439-6442

  Cao, Jia Jia ^a   Zhu, Tong Hao ^a   Wang, Shun Yi ^a   Gu, Zheng Yang ^a   Wang, Xiang ^a   Ji, Shun Jun ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 ISOCYANOBIARYL; 6 ALKYL PHENANTHRIDINE DERIVATIVE; BENZOIC ACID DERIVATIVE; DIOXANE; ISOCYANIC ACID DERIVATIVE; PERBENZOIC ACID TERT BUTYL ESTER; PHENANTHRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; SYNTHESIS;

EID: 84898933485     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc00743c     Document Type: Article

References (50)

1. J.-Q. Yu and Z.-J. Shi, Springer, 2010, vol. 292
2. I. Mkhalid, J. Barnard, T. Marder, J. Murphy, J. Hartwig, Chem. Rev., 2010, 110:890
3. T. W. Lyons, M. S. Sanford, Chem. Rev., 2010, 110:1147
4. C. S. Yeung, V. M. Dong, Chem. Rev., 2011, 111:1215
5. C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Rev., 2011, 111:1293
6. C. Liu, H. Zhang, W. Shi, A. Lei, Chem. Rev., 2011, 111:1780
7. C.-J. Li, Acc. Chem. Res., 2009, 42:335
8. X. Chen, K. M. Engle, D. Wang, J.-Q. Yu, Angew. Chem., Int. Ed., 2009, 48:5094
9. L. Ackermann, R. Vicente, A. Kapdi, Angew. Chem., Int. Ed., 2009, 48:9792
10. C. J. Scheuermann, Chem. Asian J., 2010, 5:436
11. O. Daugulis, H. Q. Do, D. Shabashov, Acc. Chem. Res., 2009, 42:1074
12. H. M. Davies, J. D. Bois, J.-Q. Yu, Chem. Soc. Rev., 2011, 40:1855
13. R. Samanta, K. Matcha, A. P. Antonchick, Eur. J. Org. Chem., 2013, 5769
14. O. Baudoin, Chem. Soc. Rev., 2011, 40:4902
15. C. Viuf, M. Bols, Angew. Chem., Int. Ed., 2001, 40:623
16. M. Baruah, M. Bols, Synlett, 2002, 1111
17. C. M. Pedersen, L. G. Marinescu, M. Bols, Org. Biomol. Chem., 2005, 3:816
18. R. Jazzar, J. Hitce, A. Renaudat, J. Sofack-Kreutzer, O. Baudoin, Chem. Eur. J., 2010, 16:2654
19. T. Wang, W. Zhou, H. Yin, J.-A. Ma, N. Jiao, Angew. Chem., Int. Ed., 2012, 51:10823
20. Z. Xie, Y. Cai, H. Hu, C. Lin, J. Jiang, Z. Chen, L. Wang, Y. Pan, Org. Lett., 2013, 15:4600
21. J. Zhao, W. Zhou, J. Han, Tetrahedron Lett., 2013, 54:6507
22. S. Pan, J. Liu, H. Li, Z. Wang, X. Guo, Z. Li, Org. Lett., 2010, 12:1932
23. L. Chen, E. Shi, Z. Liu, S. Chen, W. Wei, H. Li, K. Xu, X. Wan, Chem. Eur. J., 2011, 17:4085
24. S. Zhang, L.-N. Guo, X.-H. Duan, Org. Biomol. Chem., 2013, 11:4308
25. G. S. Kumar, B. Pieber, K. R. Reddy, C. O. Kappe, Chem. Eur. J., 2012, 18:6124
26. S.-R. Guo, Y.-Q. Yuan, J.-N. Xiang, Org. Lett., 2013, 15:4654
27. D. Liu, C. Liu, H. Li, A. Lei, Angew. Chem., Int. Ed., 2013, 52:4453
28. B. Liegault, K. Fagnou, Organometallics, 2008, 27:4841
29. S. Guin, S. K. Rout, A. Banerjee, S. Nandi, B. K. Patel, Org. Lett., 2012, 14:5294
30. X. Tan, B. Liu, X. Li, B. Li, S. Xu, H. Song, B. Wang, J. Am. Chem. Soc., 2012, 134:16163
31. R. S. Theobald, K. Schofield, Chem. Rev., 1950, 46:170
32. S. D. Phillips, R. N. Castle, J. Heterocycl. Chem., 1981, 18:223
33. P. Stevenson, K. R. Sones, M. M. Gicheru, E. K. Mwangi, Acta Trop., 1995, 59:77
34. I. Kock, D. Heber, M. Weide, U. Wolschendorf, B. Clement, J. Med. Chem., 2005, 48:2772
35. O. B. Abdel-Halim, T. Morikawa, S. Ando, H. Matsuda, M. Yoshikawa, J. Nat. Prod., 2004, 67:1119
36. C. Bailly, R. K. Arafa, F. A. Tanious, W. Laine, C. Tardy, A. Lansiaux, P. Colson, D. W. Boykin, W. D. Wilson, Biochemistry, 2005, 44:1941
37. L. Sripada, J. A. Teske, A. Deiters, Org. Biomol. Chem., 2008, 6:263
38. K. Jozwiak, S. Ravichandran, J. R. Collins, I. W. Wainer, J. Med. Chem., 2004, 47:4008
39. G. Y. Park, J. J. Wilson, Y. Song, S. J. Lippard, Proc. Natl. Acad. Sci. U. S. A., 2012, 109:11987
40. D. Nanni, P. Pareschi, C. Rizzoli, P. Sgarabotto, A. Tundo, Tetrahedron, 1995, 51:9045
41. M. Tobisu, K. Koh, T. Furukawa, N. Chatani, Angew. Chem., Int. Ed., 2012, 51:11363
42. B. Zhang, C. Mück-Lichtenfeld, C. G. Daniliuc, A. Studer, Angew. Chem., Int. Ed., 2013, 52:10792
43. Q. Wang, X. Dong, T. Xiao, L. Zhou, Org. Lett., 2013, 15:4846
44. D. Leifert, C. G. Daniliuc, A. Studer, Org. Lett., 2013, 15:6286
45. B. Zhang, C. G. Daniliuc, A. Studer, Org. Lett., 2014, 16:250
46. A. Studer, D. P. Curran, Angew. Chem., Int. Ed., 2011, 50:5018
47. B. S. Bhakuni, A. Kumar, S. J. Balkrishna, J. A. Sheikh, S. Konor, S. Kumar, Org. Lett., 2012, 14:2838
48. W.-C. Chen, Y.-C. Hsu, W.-C. Shih, T.-G. Ong, Chem. Commun., 2012, 48:6702
49. L.-P. B. Beaulieu, R. S. Roman, F. Vallee, A. B. Charette, Chem. Commun., 2012, 48:8249
50. H. Jiang, Y. Cheng, R. Wang, M. Zheng, Y. Zhang, S. Yu, Angew. Chem., Int. Ed., 2013, 52:13289