"transition-metal-free" synthesis of carbazoles by photostimulated reactions of 2′-halo[1,1′-biphenyl]-2-amines

Journal of Organic Chemistry

Volumn 80, Issue 2, 2015, Pages 928-941

  Guerra, Walter D ^a   Rossi, Roberto A ^a   Pierini, Adriana B ^a   Barolo, Silvia M ^a  

^a UNIVERSIDAD NACIONAL DE CÓRDOBA   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CHEMICAL REACTIONS; POLYCYCLIC AROMATIC HYDROCARBONS; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ARYLATIONS; C-N BOND FORMATIONS; CROSS-COUPLINGS; ISOLATED YIELD; SIMPLE PROTOCOL; SUZUKI-MIYAURA REACTION;

TRANSITION METALS;

9H CARBAZOLE; AMINE; CARBAZOLE DERIVATIVE; UNCLASSIFIED DRUG; ANILINE; ANILINE DERIVATIVE; BIPHENYL DERIVATIVE; METAL; TRANSITION ELEMENT;

ARTICLE; ARYLATION; CONTROLLED STUDY; COVALENT BOND; CROSS COUPLING REACTION; CYCLIZATION; DRUG SYNTHESIS; PHOTOSTIMULATION; SUBSTITUTION REACTION; SUZUKI REACTION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ANILINE COMPOUNDS; BIPHENYL COMPOUNDS; CARBAZOLES; CATALYSIS; METALS; MOLECULAR STRUCTURE; TRANSITION ELEMENTS;

EID: 84921369401     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5024393     Document Type: Article

References (83)

1. Lemster, T.; Pindur, U.; Lenglet, G.; Depauw, S.; Dassi, C.; Cordonnier, M. D. Eur. J. Med. Chem. 2009, 44, 3235-3252
2. Vairavelu, L.; Zeller, M.; Prasad, K. J. R. Bioorg. Chem. 2014, 54, 12-20
3. Gu, W.; Wang, S. Eur. J. Med. Chem. 2010, 45, 4692-4696
4. Zhang, F. F.; Gan, L. L.; Zhou, C. H. Bioorg. Med. Chem. Lett. 2010, 20, 1881-1884
5. Kaur, H.; Kumar, S.; Vishwakarma, P.; Sharma, M.; Saxena, K. K.; Kumar, K. Eur. J. Med. Chem. 2010, 45, 2777-2783
6. Barta, T. E.; Barabasz, A. F.; Foley, B. E.; Geng, L.; Hall, S. E.; Hanson, G. J.; Jenks, M.; Ma, W.; Rice, J. W.; Veal, J. J. Bioorg. Med. Chem. Lett. 2009, 19, 3078-3080
7. Sauerberg, P.; Pettersson, I.; Jeppesen, L.; Bury, P. S.; Mogensen, J. P.; Wassermann, K.; Brand, C. L.; Sturis, J.; Woldike, H. F.; Fleckner, J.; Andersen, S. T. J. Med. Chem. 2002, 45, 789-804
8. Sakono, K.; Ishimaru, K.; Nakamura, S. J. Antibiot. 1980, 33, 683-689
9. Hook, D. J.; Yacobucci, J. J.; OConnor, S.; Lee, M.; Kerns, E.; Krishnan, B.; Matson, J.; Hesler, G. J. Antibiot. 1990, 43, 1347-1348
10. Crich, D.; Rumthao, S. Tetrahedron 2004, 60, 1513-1516
11. Guthrie, R. W.; Brossi, A.; Mennona, F. A.; Mullin, J. G.; Kierstead, R. W.; Grunberg, E. J. Med. Chem. 1975, 18, 755-760
12. Cranwell, P. A.; Saxton, J. E. J. Chem. Soc. 1962, 3482-3487
13. Woodward, R. B.; Iacobucci, G. A.; Hochstein, F. A. J. Am. Chem. Soc. 1959, 81, 4434-4435
14. Cheng, H.-Y.; Randall, C. S.; Holl, W. W.; Constantinides, P. P.; Yue, T.-L.; Feuerstein, G. Z. Biochim. Biophys. Acta 1996, 1284, 20-28
15. Yue, T.-L.; Cheng, H.-Y.; Lysko, P. G.; McKenna, P. J.; Feuerstein, R.; Gu, J.-L.; Lysko, K. A.; Davis, L. L.; Feuerstein, G. J. Pharmacol. Exp. Ther. 1992, 263, 92-98
16. Dubois, E. A.; van den Bos, J. C.; Doornbos, T.; van Doremalen, P. A. P. M.; Somsen, G. A.; Vekemans, J. A. J. M.; Janssen, A. G. M.; Batink, H. D.; Boer, G. J.; Pfaffendorf, M.; van Royen, E. A.; van Zwieten, P. A. J. Med. Chem. 1996, 39, 3256-3262
17. Costin, B.; ODonnell, S. R.; Wanstall, J. C. J. Pharm. Pharmacol. 1983, 35, 590-592
18. Cohen, M. L.; Ruffolo, R. R., Jr.; Wiley, K. S. J. Pharmacol. Exp. Ther. 1980, 215, 325-331
19. Innis, R. B.; Corrêa, F. M. A.; Snyder, S. H. Life Sci. 1979, 24, 2255-2264
20. Boudreault, P-L. T.; Wakim, S.; Blouin, N.; Simard, M.; Tessier, C.; Tao, Y.; Leclerc, M. J. Am. Chem. Soc. 2007, 129, 9125-9136
21. Zhao, J.; Jin, T.; Islam, A.; Kwon, E.; Akhtaruzzaman, Md.; Asao, N.; Han, L.; Alamry, K. A.; Kosa, S. A.; Asiri, A. M.; Yamamoto, Y. Tetrahedron 2014, 70, 6211-6216
22. Han, L.; Zu, X.; Cui, Y.; Wu, H.; Ye, Q.; Gao, J. Org. Electron. 2014, 15, 1536-1544
23. Kawakami, S.; Ohsawa, N. Carbazole compound, light-emitting element material, organic semiconductor material, light-emitting element, light emitting device, lighting device, and electronic device. US8697885 B2, Apr 15, 2014.
24. Harada, S.; Sasaki, M. Carbazole derivative and semiconductor nanocrystal. US20130026426 A1, Jan 31, 2013.
25. Cá, N. D.; Sassi, G.; Catellani, M. Adv. Synth. Catal. 2008, 350, 2179-2182
26. Stokes, B. J.; Jovanovié, B.; Dong, H.; Richert, K. J.; Riell, R. D.; Driver, T. G. J. Org. Chem. 2009, 8, 3225-3228
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. Cho, S. H.; Yoon, J.; Chang, S. J. Am. Chem. Soc. 2011, 133, 5996-6005
29. Jiang, Q.; Duan-Mu, D.; Zhong, W.; Chen, H.; Yan, H. Chem. - Eur. J. 2013, 19, 1903-1907
30. Noji, T.; Fujiwarw, H.; Okano, K.; Tokuyama, H. Org. Lett. 2013, 15, 1946-1949
31. Gao, H.; Xu, Q-.L.; Yousufuddin, M.; Ess, D. H.; Kurti, L. Angew. Chem., Int. Ed. 2014, 53, 2701-2075
32. Budén, M. E.; Martín, S. E.; Rossi, R. A. Recent Advances in the Photoinduced Radical Nucleophilic Substitution Reactions. In CRC Handbook of Organic Photochemistry and Photobiology, 3 rd ed.; Griesbeck, A. G.; Oelgemöller, M.; Ghetti, F., Eds.; CRC Press, Inc.: Boca Raton, 2012; Chapter 15, pp 347-368.
33. RN1 Reaction. In Encyclopedia of Radicals in Chemistry, Biology & Materials, Chatgilialoglu, C.; Studer, A., Eds.; John Wiley & Sons: Chichester, 2012; pp 333-364.
34. Rossi, R. A.; Pierini, A. B.; Peñéñory, A. B. Chem. Rev. 2003, 103, 71-167
35. Rossi, R. A. Synthetic Organic Photochemistry; Griesbeck, A. G.; Mattay, J., Eds.; Marcel Dekker: New York, 2005; Vol. 12, Chapter 15, pp 495-527.
36. Bunnett, J. F. Acc. Chem. Res. 1978, 11, 413-420
37. Costentin, C.; Donati, L.; Robert, M. Chem. - Eur. J. 2009, 15, 785-792
38. Costentin, C.; Robert, M.; Savéant, J.-M. Chem. Phys. 2006, 324, 40-56
39. Budén, M. E.; Vaillard, V. A.; Martín, S. E.; Rossi, R. A. J. Org. Chem. 2009, 74, 4490-4498
40. Budén, M. E.; Rossi, R. A. Tetrahedron Lett. 2007, 48, 8739-8742
41. Budén, M. E.; Dorn, V. B.; Gamba, M.; Pierini, A. B.; Rossi, R. A. J. Org. Chem. 2010, 75, 2206-2218
42. Laha, J. K.; Barolo, S. M.; Rossi, R. A.; Cuny, G. D. J. Org. Chem. 2011, 76, 6421-6425
43. Theuns, H. G.; Lenting, H. B. M.; Salemink, C. A.; Tanaka, H.; Shibata, M.; Ito, K.; Lousberg, R. J. J. Ch. Heterocycles 1984, 22, 2007-2011
44. Roydhouse, M. D.; Walton, J. C. Chem. Commun. 2005, 4453-4455
45. Wiegand, S.; Schäfer, H. J. Tetrahedron 1995, 51, 5341-5350
46. Barolo, S. M.; Teng, X.; Cuny, G. D.; Rossi, R. A. J. Org. Chem. 2006, 71, 8493-8499
47. Soria-Castro, S.; Caminos, D. A.; Peñéñory, A. B. RSC Adv. 2014, 4, 17490-17497
48. Guastavino, J. F.; Rossi, R. J. Org. Chem. 2012, 77, 460-472
49. Tempesti, T. C.; Pierini, A. B.; Baumgartner, M. T. J. Org. Chem. 2005, 70, 6508-6511
50. Barolo, S. M.; Wang, Y.; Rossi, R. A.; Cuny, G. D. Tetrahedron 2013, 69, 5487-5494
51. Miyaura, N.; Suzuki, N. Chem. Rev. 1995, 95, 2457-2483
52. Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633-9695
53. Kostas, I. D.; Tenchiu, A.-C.; Arbez-Gindre, C.; Psycharis, V.; Paptopoulou, C. P. Catal. Commun. 2014, 51, 15-18
54. Jash, H.; Scheumann, J.; Heinrich, R. M. J. Org. Chem. 2012, 77, 10699-10706
55. Pan, X.; Wilcox, C. S. J. Org. Chem. 2010, 75, 6445-6451
56. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1998, 34, 3387-3388
57. Kudo, N.; Perseghini, M.; Fu, G. C. Angew. Chem., Int. Ed. 2006, 45, 1282-1284
58. Alonso, F.; Beletskaya, I. P.; Yus, M. Tetrahedron 2008, 64, 3047-3101
59. The reduction was carried in ethanol/water (5:2) with 1 equiv of Fe in powder and 2 equiv of HCl. See: Liu, Y.; Lu, Y.; Prashad, M.; Repic, O.; Blacklock, T. J. Adv. Synth. Catal. 2005, 347, 217-219
60. Schmidt, L. C.; Argüello, J. E.; Peñéñory, A. B. J. Org. Chem. 2007, 72, 2936-2944
61. Surry, D. S.; Buchwald, S. L. Chem. Sci. 2011, 2, 27-50
62. Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215-7216
63. Driver, M.; Hartwig, J. J. Am. Chem. Soc. 1996, 118, 7217-7218
64. Hartwig, J. F.; Shen, Q.; Ogata, T. J. Am. Chem. Soc. 2008, 130, 6586-6596
65. Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534-1544
66. Surry, D. S.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 10354-10355
67. Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338-6361
68. For experimental conditions, see: Buchwald, S. L.; Harris, M. C.; Sadlghi, J. P. Tetrahedron Lett. 1998, 39, 5327-5330
69. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
70. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100
71. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200-206
72. Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117-129
73. Miertus, S.; Tomasi, J. Chem. Phys. 1982, 65, 239-245
74. Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327-335
75. Pierini, A. B.; Vera, D. M. A. J. Org. Chem. 2003, 68, 9191-9199
76. Beugelmans, R.; Chbani, M. Bull. Soc. Chim. Fr. 1995, 132, 290-305
77. Baghbanzadeh, M.; Pilger, C.; Kappe, C. O. J. Org. Chem. 2011, 76, 1507-1510
78. Yang, W.; Zhou, J.; Wang, B.; Ren, H. Chem. - Eur. J. 2011, 17, 13665-13669
79. Hernandez-Perez, A. C.; Collins, S. K. Angew. Chem., Int. Ed. 2013, 52, 1-6
80. Zhou, Z.-Z.; Liu, F.-S.; Shen, D.-S.; Tan, C.; Luo, L.-Y. Inorg. Chem. Commun. 2011, 14, 659-662
81. Smitrovich, J. H.; Davies, I. W. Org. Lett. 2004, 6, 533-535
82. Jimenez, L. B.; Torres, N. V.; Borioni, J. L.; Pierini, A. B. Tetrahedron 2014, 70, 3614-3620
83. Mudry, C. A.; Frasca, A. R. Tetrahedron 1974, 30, 2983-2991