Substituent electronic effects govern direct intramolecular C-N cyclization of N -(biphenyl)pyridin-2-amines induced by hypervalent iodine(III) reagents

Journal of Organic Chemistry

Volumn 79, Issue 23, 2014, Pages 11395-11408

  Chu, Jean Ho ^a   Hsu, Wen Ting ^a   Wu, Yi Hua ^a   Chiang, Meng Fan ^a   Hsu, Nan Hai ^a   Huang, Hao Ping ^a   Wu, Ming Jung ^a  

^a NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CHEMICAL REACTIONS; IODINE; POLYCYCLIC AROMATIC HYDROCARBONS;

BENZIMIDAZOLES; CATION-RADICALS; ELECTRONIC EFFECTS; HYPERVALENT IODINE; N-CYCLIZATION; O-CYCLIZATION; RADICAL TRAPPING; RATIONAL MECHANISM;

CYCLIZATION;

BENZIMIDAZOLE DERIVATIVE; CARBAZOLE DERIVATIVE; IODINE; N (BIPHENYL)PYRIDIN 2 AMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; COVALENT BOND; CYCLIZATION; ORGANIC CHEMISTRY; SYNTHESIS; THIN LAYER CHROMATOGRAPHY; ULTRAVIOLET SPECTROSCOPY;

EID: 84916207805     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501822m     Document Type: Article

References (52)

1. Ricci, A., Ed. Amino Group Chemistry: From Synthesis to the Life Sciences; Wiley-VCH: Weinheim, 2008.
2. Rauws, T. R. M.; Maes, B. U. W. Chem. Soc. Rev. 2012, 41, 2463-2497
3. Chaskar, A.; Chen, H.-F.; Wong, K.-T. Adv. Mater. 2011, 23, 3876-3895
4. Bariwal, J.; Van der Eycken, E. Chem. Soc. Rev. 2013, 42, 9283-9303
5. Valente, C.; Çalimsiz, S.; Hoi, K. H.; Mallik, D.; Sayah, M.; Organ, M. G. Angew. Chem., Int. Ed. 2012, 51, 3314-3332
6. Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450-1460
7. Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400-5449
8. Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131-209
9. Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534-1544
10. Meiries, S.; LeDuc, G.; Chartoire, A.; Collado, A.; Speck, K.; Arachchige, K. S. A.; Slawin, A. M. Z.; Nolan, S. P. Chem.-Eur. J. 2013, 18, 17358-17368
11. Al-Amin, M.; Honma, T.; Hoshiya, N.; Shuto, S.; Arisawa, M. Adv. Synth. Catal. 2012, 354, 1061-1068
12. Tardiff, B. J.; McDonald, R.; Ferguson, M. J.; Stradiotto, M. J. Org. Chem. 2012, 77, 1056-1057
13. Maiti, D.; Fors, B. P.; Henderson, J. L.; Nakamura, Y.; Buchwald, S. L. Chem. Sci. 2011, 2, 57-68
14. Lundgren, R. J.; Sappong-Kumankumah, A.; Stradiotto, M. Chem.-Eur. J. 2010, 16, 1983-1991
15. Louillat, M.-L.; Patureau, F. W. Chem. Soc. Rev. 2014, 43, 901-910
16. J. Stokes, B.; Driver, T. G. Eur. J. Org. Chem. 2011, 4071-4088
17. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068-5083
18. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651-3678
19. Morofuji, T.; Shimizu, A.; Yoshida, J. J. Am. Chem. Soc. 2013, 135, 5000-5003
20. Shang, M.; Sun, S.-Z.; Dai, H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2014, 136, 3354-3357
21. Chen, X.; Hao, X.-S.; Goodhue, C. E. J.-Q.; Yu J. Am. Chem. Soc. 2006, 128, 6790-6791
22. Kawano, T.; Hirano, K.; Satoh, T.; Mirua, M. J. Am. Chem. Soc. 2010, 132, 6900-6901
23. John, A.; Nicholas, K. M. J. Org. Chem. 2011, 76, 4158-4162
24. Ng, K.-H.; Zhou, Z.; Yu, W.-Y. Org. Lett. 2012, 14, 272-275
25. Uemura, T.; Imoto, S.; Chatani, N. Chem. Lett. 2006, 35, 842-843
26. Tsang, W. C. P.; Zheng, N.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 14560-14561
27. Jordan-Hore, J. A.; Johansson, C. C. C.; Gulias, M.; Beck, E. M.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 16184-16186
28. Stokes, B. J.; Jovanović, B.; Dong, H.; Richert, K. J.; Riell, R. D.; Driver, T. G. J. Org. Chem. 2009, 74, 3225-3228
29. Youn, S. W.; Bihn, J. H.; Kim, B. S. Org. Lett. 2011, 13, 3738-3741
30. Chu, J.-H.; Lin, P.-S.; Lee, Y.-M.; Shen, W.-T.; Wu, M.-J. Chem.-Eur. J. 2011, 17, 13613-13620
31. Chu, J.-H.; Huang, H.-P.; Hsu, W.-T.; Chen, S.-T.; Wu, M.-J. Organometallics 2014, 33, 1190-1204
32. Takamatsu, K.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2014, 16, 2892-2895
33. Cho, S. H.; Yoon, J.; Chang, S. J. Am. Chem. Soc. 2011, 133, 5996-6005
34. Antonchick, A. P.; Samanta, R.; Kulikov, K.; Lategahn, J. Angew. Chem., Int. Ed. 2011, 50, 8605-8608
35. Kutsumura, N.; Kunimatsu, S.; Kagawa, K.; Otani, T.; Saito, T. Synthesis 2011, 3235-3240
36. Masters, K.-S.; Rauws, T. R. M.; Yadav, A. K.; Herrebout, W. A.; Van der Veken, B.; Maes, B. U. W. Chem.-Eur. J. 2011, 17, 6315-6320
37. Wang, H.; Wang, Y.; Peng, C.; Zhang, J.; Zhu, Q. J. Am. Chem. Soc. 2010, 132, 13217-13219
38. Huang, J.; He, Y.; Liu, L.; Zhu, Q. Chem.-Eur. J. 2012, 18, 13964-13967
39. He, Y.; Huang, J.; Liang, D.; Liu, L.; Zhu, Q. Chem. Commun. 2013, 49, 7352-7354
40. Liang, D.; He, Y.; Liu, L.; Zhu, Q. Org. Lett. 2013, 15, 3476-3479
41. Alla, S. K.; Kumar, R. K.; Sadhu, P.; Punniyamurthy, T. Org. Lett. 2013, 15, 1334-1337
42. Rao, D. N.; Rasheed, S.; Vishwakarma, R. A.; Das, P. RSC Adv. 2014, 4, 25600-25604
43. Manna, S.; Matcha, K.; Antonchick, A. P. Angew. Chem., Int. Ed. 2014, 53, 8163-8166
44. Copies of the deposited crystallographic data for CCDC-1010807 (2f) and CCDC-1010808 (2′ f) can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
45. Kita, Y.; Tohma, H.; Hatanaka, K.; Takada, T.; Fujita, S.; Mitoh, S.; Sakurai, H.; Oka, S. J. Am. Chem. Soc. 1994, 116, 3684-3691
46. Samanta, R.; Bauer, J. O.; Strohmann, C.; Antonchick, A. P. Org. Lett. 2012, 14, 5518-5521
47. Itoh, N.; Sakamoto, T.; Miyazawa, E.; Kikugawa, Y. J. Org. Chem. 2002, 67, 7424-7428
48. Liu, H.; Wang, X.; Gu, Y. Org. Biomol. Chem. 2011, 9, 1614-1620
49. ref 17 and
50. Samanta, R.; Kulikov, K.; Strohmann, C.; Antonchick, A. P. Synthesis 2012, 44, 2325-2332
51. The synthesis of substrates 4a and 4b was referenced to the following paper, see: Shi, Z.; Li, B.; Wan, X.; Cheng, J.; Fang, Z.; Cao, B.; Qin, C.; Wang, Y. Angew. Chem., Int. Ed. 2007, 46, 5554-5558
52. Yu, Z.; Ma, L.; Yu, W. Synlett 2012, 23, 1534-1540