Chinese Journal of Organic Chemistry >
Selective Oxidative Bromination of Anilines Using Potassium Bromide and ZnAl-BrO3--LDHs
Received date: 2017-05-11
Revised date: 2017-07-07
Online published: 2017-09-08
The oxidative bromination of anilines was realized with ZnAl-BrO3--LDHs/KBr as the bromine source at ambient temperature in acidic medium (AcOH/H2O). High yields of monobrominated or polybrominated anilines were achieved for a wide range of anilines. Both the substrate structure and the reaction conditions will significantly influence the reaction selectivity. The use of inexpensive reagents, environmentally benign and operationally simple process, and excellent yields make it a good alternative to the synthesis of bromoanilines.
Key words： anilines; halogenation; selectivity; aromatic substitution
Wang Ligeng , Chen Lujun , Zhang Hualong , Yu Qin . Selective Oxidative Bromination of Anilines Using Potassium Bromide and ZnAl-BrO3--LDHs[J]. Chinese Journal of Organic Chemistry, 2017 , 37(12) : 3186 -3190 . DOI: 10.6023/cjoc201705017
[1] Wischang, D.; Br€ucher, O.; Hartung, J. Chem. Rev. 2011, 255, 2204.
[2] Albadi, J.; Tajik, H.; Keshavarz, M. Monatsh. Chem. 2012, 144, 179.
[3] Butler, A.; Walker, J. V. Chem. Rev. 1993, 93, 1937.
[4] Roy, S. C.; Guin, C.; Rana, K. K.; Maiti, G. Tetrahedron Lett. 2001, 42, 6941.
[5] Stavber, S.; Jereb, M.; Zupan, M. Synthesis 2008, 1487.
[6] Venkateswarlu, K.; Suneel, K.; Das, B.; Reddy, K. N.; Reddy, T. S. Synth. Commun. 2009, 40, 215.
[7] Sammakia, T.; Stangeland, E. L.; Whitcomb, M. C. J. Org. Lett. 2002, 4, 2385.
[8] Kalyani, D.; Dick, A. R.; Anani, W. Q. Org. Lett. 2006, 8, 2523.
[9] Khan, A. T.; Goswami, P.; Choudhary, L. H. Tetrahedron Lett. 2006, 47, 2751.
[10] Zhang, G. F.; Wang, Y.; Ding, C. R.; Liu, R. H.; Liang, X. M. Chin. J. Org. Chem. 2011, 31, 804(in Chinese). (张国富, 王涌, 丁成荣, 刘仁华, 梁鑫淼, 有机化学, 2011, 31, 804.)
[11] Kikushima, K.; Moriuchi, T.; Hirao, T. Tetrahedron Lett. 2010, 41, 340.
[12] Tsoukala, A.; Liguori, L.; Occhipinti, G. Tetrahedron Lett. 2009, 50, 831.
[13] Kumar, L.; Mahajan, T.; Agarwal, D. D. Ind. Eng. Chem. Res. 2012, 51, 11593.
[14] Podgorsek, A.; Stavber, S.; Zupan, M.; Iskra, J. Tetrahedron 2009. 65, 4429.
[15] Gnaim, J. M.; Sheldon, R. A. Tetrahedron Lett. 2005, 46, 4465.
[16] Song, S.; Sun, X.; Li, X. W.; Yuan, Y. Z.; Jiao, N. Org. Lett. 2015, 17, 2886.
[17] Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
[18] Neufeldt, S. R.; Sanford, M. S. Chem. Res. 2012, 45, 936.
[19] Schroder, N.; Wencel-Delord, J.; Glorius, F. J. Am. Chem. Soc. 2012, 134, 8298.
[20] Du, Z. J.; Gao, L. X.; Lin, Y. J.; Han, F. S. ChemCatChem 2014, 6, 123.
[21] Mo, F.; Yan, J. M.; Qiu, D.; Li, F.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2010, 49, 2028.
[22] Bliman, D.; Pettersson, M.; Bood, M.; Grøtli, M. Tetrahedron Lett. 2014, 55, 2929.
[23] Brimmer, A. F.; Dahl, F. R. J. Cheminf. 2015, 71, 6112.
[24] Wang, L. G.; Zheng, F. X.; Jiang, C. X.; Ni, Z. M. J. Chin. Ceram. Soc. 2015, 43, 672(in Chinese). (王力耕, 郑飞翔, 蒋晨星, 倪哲明, 硅酸盐学报, 2015, 43, 672.)
[25] Ghiaci, M.; Sedaghat, M. E.; Ranjbari, S. Appl. Catal. A 2010, 384, 18.
[26] (a) Chrétien, J. M.; Zammattio, F.; Le Grognec, E.; Paris, M.; Cahingt, B.; Montavon, G.; Quintard, J. P. J. Org. Chem. 2005, 70, 2870.
(b) Bagmanov, B. T. Russ. J. Appl. Chem. 2009, 82, 1570.
(c) Parthasarathy, M.; Gopalakrishnan, R. Spectrochim. Acta, Part A 2012, 97, 1152.
(d) Gopal, N.; Saravanan, V. S.; Jagadeeswaran, M. Asian J. Chem. 2006, 18, 2611.
(e) Choy, J.; Jaime-Figueroa, S.; Jiang, L.; Wagner, P. Synth. Commun. 2007, 40, 3840.
(f) Trunz, B. B.; Jedrysiak, R.; Tweats, D.; Brun, R.; Kaiser, M.; Suwinski, J.; Torreele, E. Eur. J. Med. Chem. 2011, 46, 1524.
(g) Mandadapu, A. K.; Saifuddin, M.; Agarwal, P. K.; Kundu, B. Org. Biomol. Chem. 2009, 7, 2796.
(h) Glidewel, C.; Low, J. N.; Skakle, J. M.; Wardell, J. L. Acta Crystallogr., Sect. C:Cryst. Struct. Commun. 2005, C61, 336.
/
| 〈 |
|
〉 |
