Oxidative dimerization of (hetero)aromatic amines utilizing t-BuOI leading to (hetero)aromatic azo compounds: Scope and mechanistic studies

Journal of Organic Chemistry

Volumn 78, Issue 23, 2013, Pages 12090-12105

  Okumura, Sota ^a   Lin, Chun Hsuan ^a   Takeda, Youhei ^a   Minakata, Satoshi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC AMINES; AZO COMPOUND; MECHANISTIC STUDIES; OXIDATIVE DIMERIZATION; OXIDATIVE REACTION; SPECTROSCOPIC STUDIES; SYNTHETIC METHODS;

AMINES; AROMATIC COMPOUNDS; REACTION INTERMEDIATES; SPECTROSCOPIC ANALYSIS;

DIMERIZATION;

ANILINE DERIVATIVE; AROMATIC AMINE; AZO COMPOUND; HETEROAROMATIC AMINE; HETEROAROMATIC AZO COMPOUND; IODATE; IODIDE; N,N DIIODOANILINE; TERT BUTYL HYPOIODITE; UNCLASSIFIED DRUG;

AEROBIC METABOLISM; ARTICLE; DIMERIZATION; OXIDATIVE DIMERIZATION; SPECTROSCOPY; SYNTHESIS;

EID: 84890147589     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo402120w     Document Type: Article

References (83)

1. Hunger, K. Industrial Dyes: Chemistry, Properties, Applications; Wiley-VCH: Weinheim, 2003.
2. Zollinger, H. Color Chemistry: Syntheses, Properties and Applications of Organic Dyes and Pigments; VCH: New York, 1987, p 85.
3. Gordon, P. F.; Gregory, P. Organic Chemistry in Colour; Springer: New York, 1983, p 95.
4. Anderson, R. G.; Nickless, G. Analyst 1967, 92, 207
5. Zhao, Y.; He, J. Soft Matter 2009, 5, 2686
6. Barrett, C. J.; Mamiya, J.-I.; Yager, K. G.; Ikeda, T. Soft Matter 2007, 3, 1249
7. Kumar, G. S.; Neckers, D. C. Chem. Rev. 1989, 89, 1915
8. Ikeda, T. J. Mater. Chem. 2003, 13, 2037
9. Fehrentz, T.; Schönberger, M.; Trauner, D. Angew. Chem., Int. Ed. 2011, 50, 12156
10. Beharry, A. A.; Woolley, G. A. Chem. Soc. Rev. 2011, 50, 12156
11. Merino, E.; Ribagorda, M. Beilstein J. Org. Chem. 2012, 8, 1071
12. García-Amorós, J.; Velasco, D. Beilstein J. Org. Chem. 2012, 8, 1003
13. Bandara, H. M. D.; Burdette, S. C. Chem. Soc. Rev. 2011, 41, 1809
14. Merino, E. Chem. Soc. Rev. 2011, 40, 3835
15. Hamon, F.; Djedaini-Pilard, F.; Barbot, F.; Len, C. Tetrahedron 2009, 65, 10105
16. Smith, M. B.; March, J. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 5 th ed.; Wiley-Interscience: New York, 2001. For recent examples, see
17. Hu, L.; Cao, X.; Shi, L.; Qi, F.; Guo, Z.; Lu, J.; Gu, H. Org. Lett. 2011, 13, 5640
18. Sakai, N.; Fujii, K.; Nabeshima, S.; Ikeda, R.; Konakahara, T. Chem. Commun. 2010, 46, 3173
19. Farhadi, S.; Zaringhadam, P.; Sahamieh, R. Z. Acta Chim. Slov. 2007, 54, 647
20. Orito, K.; Hatakeyama, T.; Takeo, M.; Uchiito, S.; Tokuda, M.; Suginome, H. Tetrahedron 1998, 54, 8403
21. Firouzabadi, H.; Mostafavipoor, Z. Bull. Chem. Soc. Jpn. 1983, 56, 914
22. Ortiz, B.; Villanueva, P.; Walls, F. J. Org. Chem. 1972, 37, 2748
23. Baer, E.; Tosoni, A. L. J. Am. Chem. Soc. 1956, 78, 2857
24. Zhu, Y.; Shi, Y. Org. Lett. 2013, 15, 1942
25. Hu, Z.; Kerton, F. M. Org. Biomol. Chem. 2012, 10, 1618
26. Lu, W.; Xi, C. Tetrahedron Lett. 2008, 49, 4011
27. Dabbagh, H. A.; Teimouri, A.; Chermahini, A. N. Dyes Pigm. 2007, 73, 239
28. Barbero, M.; Cadamuro, S.; Dughera, S.; Giaveno, C. Eur. J. Org. Chem. 2006, 4884
29. Haghbeena, K.; Tan, E. W. J. Org. Chem. 1998, 63, 4503
30. Davey, H. H.; Lee, R. D.; Marks, T. J. J. Org. Chem. 1999, 64, 4976
31. Nutting, W. H.; Jewell, R. A.; Rapoport, H. J. Org. Chem. 1970, 35, 505
32. Grirrane, A.; Corma, A.; García, H. Nat. Protoc. 2010, 11, 429
33. Grirrane, A.; Corma, A.; García, H. Science 2008, 322, 1661
34. Cai, S.; Rong, H.; Yu, X.; Liu, X.; Wang, D.; He, W.; Li, Y. ACS Catal. 2013, 3, 478
35. Zhang, C.; Jiao, N. Angew. Chem., Int. Ed. 2010, 49, 6174
36. Ma, H.; Li, W.; Wang, J.; Xiao, G.; Gong, Y.; Qi, C.; Feng, Y.; Li, X.; Bao, Z.; Cao, W.; Sun, Q.; Veaceslav, C.; Wang, F.; Lei, Z. Tetrahedron 2012, 68, 8358
37. Takeda, Y.; Okumura, S.; Minakata, S. Angew. Chem., Int. Ed. 2012, 51, 7804
38. A featured article focusing on its experimental procedure was also published: Takeda, Y.; Okumura, S.; Minakata, S. Synthesis 2013, 45, 1029
39. Tanner, D. D.; Gidley, G. C.; Das, N.; Rowe, J. E.; Potter, A. J. Am. Chem. Soc. 1984, 106, 5261
40. Takeda, Y.; Enokijima, S.; Nagamachi, T.; Nakayama, K.; Minakata, S. Asian J. Org. Chem. 2013, 2, 91
41. Takeda, Y.; Okumura, S.; Tone, S.; Sasaki, I.; Minakata, S. Org. Lett. 2012, 14, 4874
42. Minakata, S.; Okumura, S.; Nagamachi, T.; Takeda, Y. Org. Lett. 2011, 13, 2966
43. Minakata, S.; Sasaki, I.; Ide, T. Angew. Chem., Int. Ed. 2010, 49, 1309
44. Minakata, S.; Morino, Y.; Ide, T.; Oderaotoshi, Y.; Komatsu, M. Chem. Commun. 2007, 3279
45. Minakata, S.; Morino, Y.; Oderaotoshi, Y.; Komatsu, M. Chem. Commun. 2006, 3337
46. Minakata, S.; Morino, Y.; Oderaotoshi, Y.; Komatsu, M. Org. Lett. 2006, 8, 3335
47. Castro, M. C. R.; Schellenberg, P.; Belsley, M.; Fonseca, A. M. C.; Fernandes, S. S. M.; Raposo, M. M. M. Dyes Pigm. 2012, 95, 392
48. Raposo, M. M. M.; Castro, M. C. R.; Fonseca, A. M. C.; Schellenberg, P.; Belsley, M. Tetrahedron 2011, 67, 5189 and references therein
49. Wendler, T.; Schütt, C.; Näther, C.; Herges, R. J. Org. Chem. 2012, 77, 3284 and references therein
50. Iranpoor, N.; Firouzabadi, H.; Shahin, R.; Khalili, D. Synth. Commun. 2012, 42, 2040
51. Iranpoor, N.; Firouzabadi, H.; Khalili, D. Bull. Chem. Soc. Jpn. 2010, 83, 923
52. Iranpoor, N.; Firouzabadi, H.; Khalili, D. Org. Biomol. Chem. 2010, 8, 4436
53. Samanta, S.; Beharry, A. A.; Sadovski, O.; McCormick, T. M.; Babalhavaeji, A.; Tropepe, V.; Woolley, A. J. Am. Chem. Soc. 2013, 135, 9777
54. Bléger, D.; Schwarz, J.; Brouwer, A. M.; Hecht, S. J. Am. Chem. Soc. 2012, 134, 20597
55. 13C NMR Spectroscopy; Elsevier Science: Amsterdam, 2005.
56. Gottardi, W. Monatsh. Chem. 1975, 106, 1019
57. Gottardi, W. Monatsh. Chem. 1974, 105, 611
58. Lamer, A. A.; Nicholas, K. M. J. Org. Chem. 2010, 75, 7644
59. Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543
60. Zard, S. Z. Synlett 1996, 1148
61. Stella, L. Angew. Chem., Int. Ed. Engl. 1983, 22, 337
62. Danen, W. C.; Neugebauer, F. A. Angew. Chem., Int. Ed. Engl. 1975, 14, 783
63. Neale, R. S. Synthesis 1971, 1
64. Glover, S. A.; Goosen, A.; Venter, R. D. S. Afr. J. Chem 1978, 31, 33
65. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165
66. Beale, T. M.; Chudzinski, M. G.; Sarwar, M. G.; Taylor, M. S. Chem. Soc. Rev. 2013, 42, 1667
67. Erdélyi, M. Chem. Soc. Rev. 2012, 41, 3547
68. Fourmigué, M. Curr. Opin. Solid State Mater. Sci 2009, 13, 36
69. Metrangolo, P.; Meyer, F.; Pilati, T.; Resnati, G.; Terraneo, G. Angew. Chem., Int. Ed. 2008, 47, 6114
70. Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Acc. Chem. Res. 2005, 38, 386
71. Auffinger, P.; Hays, F. A.; Westhof, E.; Ho, P. S. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 16789
72. Metrangolo, P.; Resnati, G. Chem.-Eur. J. 2001, 7, 2511
73. Glover, S. A. Tetrahedron 1998, 54, 7229
74. Thorwirth, R.; Bernhardt, F.; Stolle, A.; Ondruschka, B.; Asghari, J. Chem.-Eur. J. 2010, 16, 13236
75. Hrobárik, P.; Hrobáriková, V.; Sigmundová, I.; Zahradník, P.; Fakis, M.; Polyzos, I.; Persephonis, P. J. Org. Chem. 2011, 76, 8726
76. Serdons, K.; Laera, K. V.; Janssen, P.; Kung, H. F.; Bormans, G.; Verbruggen, A. J. Med. Chem. 2009, 52, 7090
77. Hadjiarapoglou, L.; Spyroudis, S.; Varvoglis, A. Synthesis 1983, 207
78. Dolenc, D. Synlett 2000, 544
79. Lim, Y.-K.; Lee, K.-S.; Cho, C.-G. Org. Lett. 2003, 5, 979
80. Matsui, M.; Shirai, K.; Tanaka, N.; Funabiki, K.; Muramatsu, H.; Shibata, K.; Abe, Y.; Ohgomori, Y. J. Mater. Chem. 1999, 9, 2755
81. Liang, T.-Y.; Schuster, G. B. J. Am. Chem. Soc. 1987, 109, 7803
82. Leyva, E.; Medina, C.; Moctezuma, E.; Leyva, S. Can. J. Chem. 2004, 82, 1712
83. Meesala, R.; Nagarajan, R. Tetrahedron 2009, 65, 6050