Citation: CHEN Sheng, HAN Jian-Lin*, LI Gui-Gen, PAN Yi*. K₂CO₃/Ni(OAc)₂ Catalyzed Aminobromination of β-Methyl-β-nitrostyrenes with Benzamide/N, N-Dibromobenzamide as Nitrogen/Bromine Source[J]. Chinese Journal of Inorganic Chemistry, ;2014, 30(1): 213-219. doi: 10.11862/CJIC.2014.042 shu

K₂CO₃/Ni(OAc)₂ Catalyzed Aminobromination of β-Methyl-β-nitrostyrenes with Benzamide/N, N-Dibromobenzamide as Nitrogen/Bromine Source

CHEN Sheng ¹ ,
HAN Jian-Lin* ^1,2 ,
LI Gui-Gen ^2,3 ,
PAN Yi* ^1,2

1.
1 School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination, Nanjing University, Nanjing 210093, China;

Received Date: 24 June 2013
Available Online: 24 October 2013
Fund Project:

An efficient and facile aminobromination reaction of β-methyl-β-nitrostyrenes with PhCONH₂/PhCONBr₂ as nitrogen/bromine source has been developed, which could tolerate a wide scope of substrates with good chemical yield and diastereoselectivity. This aminobrominaiton system uses metal salt and base as the co-catalyst, which is different from our previous reported systems.
- aminobromination;benzamide;β-methyl-β-nitrostyrenes;haloamines,
1. [1]
  [1] Kemp J E. Comprehensive Organic Synthesis: Vol.3; Trost B M, Fleming I, Eds.; Oxford: Pergamon Press, 1991:469-513
2. [2]
  [2] Yeung Y Y, Gao X, Corey E J. J. Am. Chem. Soc., 2006, 128:9644-9645
3. [3]
  [3] Griffith D A, Danishefsky S J. J. Am. Chem. Soc., 1991, 113: 5863-5864
4. [4]
  [4] Lessard J, Driguez H, Vermes J P. Tetrahedron Lett., 1970, 11:4887-4891
5. [5]
  [5] Daniher F A, Butler P E. J. Org. Chem., 1968, 33:4336-4340
6. [6]
  [6] Orlek B S, Stemp G. Tetrahedron Lett., 1991, 32:4045-4048
7. [7]
  [7] Manzoni M R, Zabawa T P, Kasi D, et al. Organometallics, 2004, 23:5618-5621
8. [8]
  [8] Danielec H, Klugge J, Schlummer B, et al. Synthesis, 2006: 551-556
9. [9]
  [9] Xu L, Du H F, Shi Y. J. Org. Chem., 2007, 72:7038-7041
10. [10]
  [10] Du H F, Zhao B G, Shi Y. J. Am. Chem. Soc., 2007, 129: 762-763
11. [11]
  [11] Li G, Saibabu Kotti S R S, Timmons C. Eur. J. Org. Chem., 2007:2745-2758
12. [12]
  [12] Qui J, Silverman R B. J. Med. Chem., 2000, 43:706-720
13. [13]
  [13] Chen D, Timmons C, Guo L, et al. Synthesis, 2004:2749-2784
14. [14]
  [14] Chen D, Kim S H, Hodges B, et al. ARKIVOC, 2003(xii): 56-62
15. [15]
  [15] Chen D, Guo L, Liu J, et al. Org. Lett., 2005, 7:921-924
16. [16]
  [16] Mei H B, Yan L J, Han J L, et al. Chem. Biol. Drug Des., 2010, 76:392-396
17. [17]
  [17] Zhang G Q, An G H, Zheng J, et al. Tetrahedron Lett., 2010, 51:987-989
18. [18]
  [18] Li G, Wei H X, Kim S H, et al. Org. Lett., 1999, 1:395-397
19. [19]
  [19] Wei H X, Kim S H, Li G. Tetrahedron, 2001, 57:3869-3871
20. [20]
  [20] Han J L, Zhi S J, Wang L Y, et al. Eur. J. Org. Chem., 2007: 1332-1337
21. [21]
  [21] Sun H, Zhang G Q, Zhi S J, et al. Org. Biol. Chem., 2010, 8: 4236-4239
22. [22]
  [22] Chen Z G, Wei J F, Li R T, et al. J. Org. Chem., 2009, 74: 1371-1373
23. [23]
  [23] Thakur V V, Talluri S K, Sudalai A. Org. Lett., 2003, 5:861-864
24. [24]
  [24] Wu X L, Xia J J, Wang G W. Org. Biomol. Chem., 2008, 6: 548-553
25. [25]
  [25] Wei J F, Zhang L H, Chen Z G, et al. Org. Biomol. Chem., 2009, 7:3280-3284
26. [26]
  [26] Li W L, Chen Z G, Zhou J M, et al. Chin. J. Chem., 2012, 30:830-836
27. [27]
  [27] Qi M H, Shao L X, Shi M. Chin. J. Chem., 2011, 29:2739-2743
28. [28]
  [28] Zhi S J, Han J L, Lin C, et al. Synthesis, 2008:1570-1574
29. [29]
  [29] Zhi S J, Sun H, Lin C, et al. Sci. China Chem., 2010, 53: 140-146
30. [30]
  [30] Zhi S J, Mei H B, Zhang G Q, et al. Sci. China Chem., 2010, 53:1946-1952
31. [31]
  [31] Qian Y, Ji X Y, Zhou W, et al. Tetrahedron, 2012, 68:6198-6203
32. [32]
  [32] Mei H B, Han J L, Li G, et al. RSC Adv., 2011, 1:429-433
33. [33]
  [33] Mei H B, Xiong Y W, Qian Y, et al. RSC Adv., 2012, 2:151-155
34. [34]
  [34] Ji X Y, Mei H B, Qian Y, et al. Synthesis, 2011:3680-3686
35. [35]
  [35] Ji X Y, Duan Z Q, Qian Y, et al. RSC Adv., 2012, 2:5565-5570
36. [36]
  [36] Chen Z G, Zhao P F, Wang Y. Eur. J. Org. Chem., 2011: 5887-5893
37. [37]
  [37] Chen Z G, Wang Y, Wei J F, et al. J. Org. Chem., 2010, 75: 2085-2088
38. [38]
  [38] Zhi S J, Sun H, Zhang G Q, et al. Org. Biomol. Chem., 2010, 8:628-631
39. [39]
  [39] Zhi S J, An G H, Sun H, et al. Tetrahedron Lett., 2010, 51: 2745-2747
40. [40]
  [40] Enders D, Wiedemann J. Synthesis, 1996:1443-1450
41. [41]
  [41] Lucet D, Toupet L, Gall T L, et al. J. Org. Chem., 1997, 62: 2682-2683
42. [42]
  [42] Chen S, Han J L, Li G G, et al. Tetrahedron Lett., 2013, 54: 2781-2784
43. [43]
  [43] Chudasama V, Wilden J D. Chem. Commun., 2008:3768-3770
44. [44]
  [44] Ferjancic Z, Matovic R, Saicic R N. Tetrahedron, 2006, 62: 8503-8514
1. [1]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
2. [2]
  Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
3. [3]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
4. [4]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
5. [5]
  Tiantian MA , Sumei LI , Chengyu ZHANG , Lu XU , Yiyan BAI , Yunlong FU , Wenjuan JI , Haiying YANG . Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 725-735. doi: 10.11862/CJIC.20230351
6. [6]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
7. [7]
  Xiuyun Wang , Jiashuo Cheng , Yiming Wang , Haoyu Wu , Yan Su , Yuzhuo Gao , Xiaoyu Liu , Mingyu Zhao , Chunyan Wang , Miao Cui , Wenfeng Jiang . Improvement of Sodium Ferric Ethylenediaminetetraacetate (NaFeEDTA) Iron Supplement Preparation Experiment. University Chemistry, 2024, 39(2): 340-346. doi: 10.3866/PKU.DXHX202308067
8. [8]
  Yongpo Zhang , Xinfeng Li , Yafei Song , Mengyao Sun , Congcong Yin , Chunyan Gao , Jinzhong Zhao . Synthesis of Chlorine-Bridged Binuclear Cu(I) Complexes Based on Conjugation-Driven Cu(II) Oxidized Secondary Amines. University Chemistry, 2024, 39(5): 44-51. doi: 10.3866/PKU.DXHX202309092
9. [9]
  Meijin Li , Xirong Fu , Xue Zheng , Yuhan Liu , Bao Li . The Marvel of NAD⁺: Nicotinamide Adenine Dinucleotide. University Chemistry, 2024, 39(9): 35-39. doi: 10.12461/PKU.DXHX202401027
10. [10]
  Hong Zheng , Xin Peng , Chunwang Yi . The Tale of Caprolactam Cyclic Oligomers: The Ever-changing Life of “Princess Cyclo”. University Chemistry, 2024, 39(9): 40-47. doi: 10.12461/PKU.DXHX202403058
11. [11]
  Yuena Yu , Fang Fang . Microwave-Assisted Synthesis of Safinamide Methanesulfonate. University Chemistry, 2024, 39(11): 210-216. doi: 10.3866/PKU.DXHX202401076
12. [12]
  Xinghai Li , Zhisen Wu , Lijing Zhang , Shengyang Tao . Machine Learning Enables the Prediction of Amide Bond Synthesis Based on Small Datasets. Acta Physico-Chimica Sinica, 2025, 41(2): 100010-. doi: 10.3866/PKU.WHXB202309041
13. [13]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
14. [14]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
15. [15]
  Xueli Mu , Lingli Han , Tao Liu . Quantum Chemical Calculation Study on the E2 Elimination Reaction of Halohydrocarbon: Designing a Computational Chemistry Experiment. University Chemistry, 2025, 40(3): 68-75. doi: 10.12461/PKU.DXHX202404057
16. [16]
  Hongsheng Tang , Yonghe Zhang , Dexiang Wang , Xiaohui Ning , Tianlong Zhang , Yan Li , Hua Li . A Wonderful Journey through the Kingdom of Hazardous Chemicals. University Chemistry, 2024, 39(9): 196-202. doi: 10.12461/PKU.DXHX202403098
17. [17]
  Ling Liu , Haibin Wang , Genrong Qiang . Curriculum Ideological and Political Design for the Comprehensive Preparation Experiment of Ethyl Benzoate Synthesized from Benzyl Alcohol. University Chemistry, 2024, 39(2): 94-98. doi: 10.3866/PKU.DXHX202304080
18. [18]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
19. [19]
  Wanmin Cheng , Juan Du , Peiwen Liu , Yiyun Jiang , Hong Jiang . Photoinitiated Grignard Reagent Synthesis and Experimental Improvement in Triphenylmethanol Preparation. University Chemistry, 2024, 39(5): 238-242. doi: 10.3866/PKU.DXHX202311066
20. [20]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(733)
HTML views(85)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

K2CO3/Ni(OAc)2 Catalyzed Aminobromination of β-Methyl-β-nitrostyrenes with Benzamide/N, N-Dibromobenzamide as Nitrogen/Bromine Source

Metrics

通讯作者: 陈斌, bchen63@163.com

K₂CO₃/Ni(OAc)₂ Catalyzed Aminobromination of β-Methyl-β-nitrostyrenes with Benzamide/N, N-Dibromobenzamide as Nitrogen/Bromine Source