Selective Oxidative Bromination of Anilines Using Potassium Bromide and ZnAl-BrO3--LDHs

doi:10.6023/cjoc201705017

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (12): 3186-3190.DOI: 10.6023/cjoc201705017 Previous Articles Next Articles

Articles

ZnAl-BrO₃^--LDHs/KBr溴源在苯胺类化合物选择性氧化溴代的应用

王力耕, 陈璐焌, 章华隆, 余琴

浙江工业大学化学工程学院杭州 310014

收稿日期:2017-05-11 修回日期:2017-07-07 发布日期:2017-09-08
通讯作者: 王力耕 E-mail:wanglg@zjut.edu.cn

Selective Oxidative Bromination of Anilines Using Potassium Bromide and ZnAl-BrO₃^--LDHs

Wang Ligeng, Chen Lujun, Zhang Hualong, Yu Qin

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Received:2017-05-11 Revised:2017-07-07 Published:2017-09-08
Contact: 10.6023/cjoc201705017 E-mail:wanglg@zjut.edu.cn

1. Selective Oxidative Bromination of Anilines Using Potassium Bromide and ZnAl-BrO₃^--LDHs.PDF(1728KB)

Abstract

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

Cite this article

Wang Ligeng, Chen Lujun, Zhang Hualong, Yu Qin. Selective Oxidative Bromination of Anilines Using Potassium Bromide and ZnAl-BrO₃^--LDHs[J]. Chin. J. Org. Chem., 2017, 37(12): 3186-3190.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[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.

ZnAl-BrO₃^--LDHs/KBr溴源在苯胺类化合物选择性氧化溴代的应用

Selective Oxidative Bromination of Anilines Using Potassium Bromide and ZnAl-BrO₃^--LDHs

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Yatong Fu, Chaofan Sun, Dan Zhang, Chengguo Jin, Juyou Lu. Recent Progress in B—H Bond Functionalization of nido-Carboranes [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 438-447.
[2]	Jian Zhang, Wanjie Liang, Yi Yang, Fachao Yan, Hui Liu. Regiocontrollable Difunctionalization of N-Allenamines [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 335-348.
[3]	Yingzhen Zhang, Dandan Jiang, Juanhua Li, Jingjing Wang, Kunming Liu, Jinbiao Liu. Construction Strategy and Imaging of Highly Selective Selenocysteine Fluorescent Probes [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 41-53.
[4]	Jingrui Wang, Yongkui Feng, Nengzhong Wang, Nianyu Huang, Hui Yao. Pd-Catalyzed Stereoselective Synthesis of Nitroalkyl β-C-Glycosides [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3216-3225.
[5]	Yaxin Liu, Yu Zhang, Shuping Luo. Design and Synthesis of Thermal Delayed Fluorescence (TADF) Photocatalyst and Its Photocatalytic Dehalogenation Performance [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2476-2483.
[6]	Zhou Zhang, Yu Guo, Jing Yang, Dan Wu, Jiaxin Wang, Xinyue Hong, Peijun Cai, Liangce Rong. Electrochemically Promoted Halogenation of Imidazoland-[1,2-a]pyridine with Dichloro(bromo)ethylene and Iodoform [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2104-2109.
[7]	Xiaojing Hu, Feixiang Guo, Runqing Zhu, Bingqi Zhou, Tao Zhang, Lizhen Fang. Synthesis of p-Alkoxy Phenol and Its Application after Dearomatization [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2239-2244.
[8]	Wang Jiang, Zhuangzhi Shi. Recent Progress in meta-/para-Selective Aromatic C—H Borylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1691-1705.
[9]	Jian Ji, Jinhua Liu, Cong Guan, Xuwen Chen, Yun Zhao, Shunying Liu. High Regioselective Synthesis of N²-Substituted-1,2,3-triazole via N-Sulfonyl-1,2,3-triazole Coupling with Alcohol Catalyzed by in-situ Generated Sulfonic Acid [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1168-1176.
[10]	Xun Xiang, Zhaolin He, Xiuqin Dong. Recent Advances of Efficient Synthesis of Chiral Molecules Promoted by Pd/Chiral Phosphoric Acid Synergistic Catalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 791-808.
[11]	Ping Guo, Yong Zhou, Jie Zhao. Z∶E Selective Preparation of Disubstituted Internal Alkenes and Trisubstituted Alkenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 855-872.
[12]	Chunbo Dai, Siqi Xia, Xiaoyu Chen, Limin Yang. N-Heterocyclic Carbene (NHC)-Catalyzed [4+3] Cycloaddition to Synthesize 4-Aminobenzoheptenolactons [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1084-1090.
[13]	Menghan Shen, Laiqiang Li, Quan Zhou, Jiehui Wang, Lei Wang. Visible-Light-Induced Regio-selective Oxidative Coupling of Quinoxalinones with Pyrrole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 697-704.
[14]	Jing Sun, Mengmeng Zhang, Xiaolong Guo, Qi Wang, Luyao Wang. Synthesis of Diaryl Selenium Compounds without Transition-Metal Catalyst [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4251-4260.
[15]	Kang Pan, Fan Xu. Lanthanum Silylamide-Catalyzed Synthesis of Enol Phosphates [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4261-4267.

ZnAl-BrO3--LDHs/KBr溴源在苯胺类化合物选择性氧化溴代的应用