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

  • 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.
  • 加载中
    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

  • 加载中
    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 XiongN-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 LUOPintian ZOUXiaoyan WANGZheng LIUXiangfei KONGQun TANGSheng 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 MASumei LIChengyu ZHANGLu XUYiyan BAIYunlong FUWenjuan JIHaiying 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 Bai1H 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

Metrics
  • PDF Downloads(0)
  • Abstract views(730)
  • 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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return