Citation: Mao Yu, Tian Shaixiao, Zhang Wei, Xu Guangyu. Preparation and Application of Vinamidinium Salts in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, ;2016, 36(4): 700-710. doi: 10.6023/cjoc201511008 shu

Preparation and Application of Vinamidinium Salts in Organic Synthesis

  • Corresponding author: Xu Guangyu, 
  • Received Date: 3 November 2015
    Available Online: 2 December 2015

    Fund Project: 湖南省医药卫生科研计划课题(No.B2013-050)资助项目. (No.B2013-050)

  • As a kind of important three-carbon building block, vinamidinium salts have been widely used in organic synthesis. In this paper the synthetic methods of vinamidinium salts are summarized, and its applications in the synthesis of aldehydes, aromatic and heterocyclic compounds in recent years are reviewed.
  • 加载中
    1. [1]

      [1] Nair, V.; Cooper, C. S. J. Org. Chem. 1981, 46, 4759.

    2. [2]

      [2] Lloyd, D.; Hamish, M. Angew. Chem., Int. Ed. 1976, 15, 459.

    3. [3]

      [3] Coverdale, H. A.; Hsung, R. P. Chemtracts 2003, 16, 238.

    4. [4]

      [4] Arnold, Z. Coll. Czech. Chem. Commun. 1965, 30, 2125.

    5. [5]

      [5] Davies, I. W.; Marcoux, J-F.; Wu, J.; Palucki, M.; Corley, E. G.; Robbins, M. A.; Tsou, N.; Ball, R. G.; Dormer, P.; Larsen, R. D.; Reider, P. J. J. Org. Chem. 2000, 65, 4571.

    6. [6]

      [6] Davies, I. W.; Marcoux, J.-F.; Wu, J.; Dormer, P. G.; Hughes, D.; Reider, P. J. J. Org. Chem. 2001, 66, 251.

    7. [7]

      [7] Davies, I. W.; Tellers, D. M.; Shultz, S.; Fleitz, F. J.; Cai, D. W.; Sun, Y. K. Org. Lett. 2002, 4, 2969.

    8. [8]

      [8] Davies, I. W.; Marcoux, J.-F.; Taylor, J. Org. Synth. 2003, 80, 200.

    9. [9]

      [9] Selvi, S.; Perumal, P. T. Tetrahedron Lett. 1997, 38, 6263.

    10. [10]

      [10] Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Dwornik, K. A.; Petrich, S. A.; Du, K. X.; Bruce, M. A.; Vu, P.; Vargas, M.; Keertikar, K. M.; Hosein, K. N.; Jones, C. R.; Sikorski, J. A. Tetrahedron 1998, 54, 5075.

    11. [11]

      [11] Wang, X.; Gao, J.; Weng, Y. Zhejiang Chem. Ind. 2012, 43, 14 (in Chinese). (汪霞, 高洁婷, 翁意意, 浙江化工, 2012, 43, 14.)

    12. [12]

      [12] Král, V.; Dvořák, D. Tetrahedron Lett. 1982, 23, 1725.

    13. [13]

      [13] Arnold, Z.; Buděšinský, M. J. Org. Chem. 1988, 53, 5352.

    14. [14]

      [14] Gupton, J. T.; Norman, B.; Wysong, E. Synth. Commun. 1985, 15, 1305.

    15. [15]

      [15] Gupton, J. T.; Riesinger, S. W.; Shah, A. S.; Gall, J. E.; Bevirt, K. M. J. Org. Chem. 1991, 56, 976.

    16. [16]

      [16] Yamanaka, H.; Hisaki, K.; Kase, K.; Ishihara, T. Tetrahedron Lett. 1998, 39, 4355.

    17. [17]

      [17] Davies, I. W.; Marcoux, J.-F.; Taylor, J. D. O.; Dormer, P. G.; Deeth, R. J.; Marcotte, F.-A.; Hughes, D. L.; Reider. P. J. Org. Lett. 2002, 4, 439.

    18. [18]

      [18] Davies, I. W.; Marcoux, J.-F.; Taylor, J. D. O.; Dormer, P. G.; Deeth, R. J.; Marcotte, F.-A.; Hughes, D. L.; Reider. P. J. J. Org. Chem.2004, 69, 1298.

    19. [19]

      [19] Jutz, V. C.; Wagner, R. M. Angew. Chem., Int. Ed. 1972, 84, 2992.

    20. [20]

      [20] Anderson, Jr., A. G.; Daugs, E. D.; Kao, L. G.; Wang, J.-F. J. Org. Chem. 1986, 51, 2961.

    21. [21]

      [21] Church, R.; Trust, R.; Albright, J. D.; Powell, D. W. J. Org. Chem. 1995, 60, 3750.

    22. [22]

      [22] Marcoux, J.-F.; Corley, E. G.; Rossen, K.; Pye, P.; Wu, J.; Robbins, M. A.; Davies, I. W.; Larsen, R. D.; Reider, P. J. J. Org. Lett. 2000, 2, 2339.

    23. [23]

      [23] Marcoux, J.-F.; Marcotte, F.-A.; Wu, J.; Dormer, P. G.; Davies, I. W.; Hughes, D.; Reider, P. J. J. Org. Chem.2001, 66, 4194.

    24. [24]

      [24] Guo, H.; Kang, C.; Qiu, X.; Jin, R.; Gao, L. Chin. J. Appl. Chem. 2005, 22, 462 (in Chinese). (郭海泉, 康传清, 邱雪鹏, 金日哲, 高连勋, 应用化学, 2005, 22, 462.)

    25. [25]

      [25] Wypych, J.-C.; Nguyen, T. M.; Bénéchie, M.; Marazano, C. J. Org. Chem. 2008, 73, 1169.

    26. [26]

      [26] Cho, I. S.; Gong, L. Y.; Muchowski, J. M. J. Org. Chem. 1991, 56, 7288.

    27. [27]

      [27] Zhang, X. H.; Zhong, W.; Li, X. Z.; Li, S. Chin. Chem. Lett. 2009, 20, 771.

    28. [28]

      [28] Shi, X. F.; Ishihara, T.; Yamanaka, H. Tetrahedron Lett. 1995, 36, 1527.

    29. [29]

      [29] Yamanaka, H.; Takekawa, T.; Morita, K.; Ishihara, T. Tetrahedron Lett. 1996, 37, 1829.

    30. [30]

      [30] Frutos, R. P.; Wei, X. D.; Patel, N. D.; Tampone, T. G.; Mulder, J. A.; Busacca, C. A.; Senanayake, C. H. J. Org. Chem. 2013, 78, 5800.

    31. [31]

      [31] Gupton, J. T.; Miller, R. B.; Krumpe, K. E.; Clough, S. C.; Banner, E. J.; Kanters, R. P. F.; Du, K. X.; Keertikar, K. M.; Lauerman, N. E.; Solano, J. M.; Adams, B. R.; Callahan, D. W.; Little, B. A.; Scharf, A. B.; Sikorski, J. A. Tetrahedron 2005, 61, 1845.

    32. [32]

      [32] Gupton, J. T.; Krolikowski, D. A.; Yu, R. H.; Riesinger, S. W. J. Org. Chem. 1990, 55, 4735.

    33. [33]

      [33] Smith, S. Q.; Dudek, S. T.; He, S. H.; Girod, J. A.; Nunes, S. R. Tetrahedron Lett. 2013, 54, 3965.

    34. [34]

      [34] Clemens, R. T.; Smith, S. Q. Tetrahedron Lett. 2005, 46, 1319.

    35. [35]

      [35] Yamanaka, H.; Takekawa, T.; Morita, K.; Ishihara, T. Tetrahedron Lett. 1996, 37, 1829.

    36. [36]

      [36] Gupton, J. T.; Wilkinson, D. R.; Sikorski, J. A.; Clough, S. C.; Miller, R. B.; Norwood, B. K. H.; Chertudi, I. B.; Hickenboth, C. R.; Cutro, S. R.; Petrich, S. A.; Hicks, F. A. Tetrahedron 2002, 58, 5467.

    37. [37]

      [37] Gupton, J. T.; Telang, N.; Gazzo, D. F.; Barelli, P. J.; Lescalleet, K. E.; Fagan, J. W.; Mills, B. J.; Finzel, K. L.; Kanters, R. P. F.; Crocker, K. R.; Dudek, S. T.; Lariviere, C. M.; Smith, S. Q.; Keertikar, K. M. Tetrahedron 2013, 69, 5829.

    38. [38]

      [38] Petrich, S. A.; Qian, Z. R.; Santiago, L. Y.; Gupton, J. T.; Sikorski, J. A. Tetrahedron 1994, 50, 12113.

    39. [39]

      [39] Angus. R. O.; Bryce, M. R.; Keshavarz-K, M.; Wudl, F. Synthesis 1988, 746.

    40. [40]

      [40] Mehranpour, A. M.; Hashemnia, S.; Shayan, Z. Synth. Commun. 2011, 41, 3501.

    41. [41]

      [41] Quast, H.; Seidenspinner, H.-M.; Stawitz, J. W. Eur. J. Org. Chem. 2013, 4852.

    42. [42]

      [42] Mehranpour, A. M.; Hashemnia, S.; Bashiri, E. Synth. Commun. 2013, 43, 1931.

    43. [43]

      [43] Mehranpour, A. M. Tetrahedron Lett. 2014, 55, 5229.

    44. [44]

      [44] Zhou, S.; Larios, E. S.; Gravel, M. J. Org. Chem. 2012, 77, 3576.

  • 加载中
    1. [1]

      Lingqi Zhang Hairong Huang Jialin Li Li Ji Yufan Pan Meiling Ye Cuixue Chen Shunü Peng . 桂花碳量子点的绿色制备及科普应用方案. University Chemistry, 2025, 40(8): 298-306. doi: 10.12461/PKU.DXHX202409138

    2. [2]

      Shuhui Li Rongxiuyuan Huang Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028

    3. [3]

      Qiuping Liu Yongxian Fan Wenxian Chen Mengdi Wang Mei Mei Genrong Qiang . Design of Ideological and Political Education for the Preparation Experiment of Ferrous Sulfate. University Chemistry, 2024, 39(2): 116-120. doi: 10.3866/PKU.DXHX202309083

    4. [4]

      Fengxiao Wang Zhiwei Miao Yaofeng Yuan . 有机磷化学与化学教学. University Chemistry, 2025, 40(8): 158-168. doi: 10.12461/PKU.DXHX202410077

    5. [5]

      Yongjian Zhang Fangling Gao Hong Yan Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035

    6. [6]

      Aidang Lu Yunting Liu Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029

    7. [7]

      Yongming Guo Jie Li Chaoyong Liu . Green Improvement and Educational Design in the Synthesis and Characterization of Silver Nanoparticles. University Chemistry, 2024, 39(3): 258-265. doi: 10.3866/PKU.DXHX202309057

    8. [8]

      Yufan Pan Xue Ding Jiayu Lin Haiting Wu Hairong Huang Cuixue Chen Meiling Ye . Oil Cosmetics, Charming Chemistry: A Gradient Science Popularization Scheme for Cream Cosmetic Preparation. University Chemistry, 2025, 40(4): 382-389. doi: 10.12461/PKU.DXHX202406078

    9. [9]

      Xinzhe HUANGLihui XUYue YANGLiming WANGZhangyong LIUZhongjian WANG . Preparation and visible light responsive photocatalytic properties of BiSbO4/BiOBr. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 284-292. doi: 10.11862/CJIC.20240212

    10. [10]

      Tiantian Zheng Huiyi Wang Huimin Li Xuanhe Liu Hong Shang . Anti-Counterfeiting National Salvation Chronicle of 006. University Chemistry, 2024, 39(9): 254-258. doi: 10.3866/PKU.DXHX202307032

    11. [11]

      Wenli FENGLu ZHAOYunfeng BAIFeng FENG . Research progress on ultralong room temperature phosphorescent carbon dots. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 833-846. doi: 10.11862/CJIC.20240308

    12. [12]

      Yuanyin CuiJinfeng ZhangHailiang ChuLixian SunKai Dai . Rational Design of Bismuth Based Photocatalysts for Solar Energy Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2405016-0. doi: 10.3866/PKU.WHXB202405016

    13. [13]

      Shiyan Cheng Yonghong Ruan Lei Gong Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024

    14. [14]

      Miaomiao He Zhiqing Ge Qiang Zhou Jiaqing He Hong Gong Lingling Li Pingping Zhu Wei Shao . Exploring the Fascinating Realm of Quantum Dots. University Chemistry, 2024, 39(6): 231-237. doi: 10.3866/PKU.DXHX202310040

    15. [15]

      Laiying Zhang Yaxian Zhu . Exploring the Silver Family. University Chemistry, 2024, 39(9): 1-4. doi: 10.12461/PKU.DXHX202409015

    16. [16]

      Yuanpei ZHANGJiahong WANGJinming HUANGZhi HU . Preparation of magnetic mesoporous carbon loaded nano zero-valent iron for removal of Cr(Ⅲ) organic complexes from high-salt wastewater. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1731-1742. doi: 10.11862/CJIC.20240077

    17. [17]

      Xinyu Zhu Meili Pang . Application of Functional Group Addition Strategy in Organic Synthesis. University Chemistry, 2024, 39(3): 218-230. doi: 10.3866/PKU.DXHX202308106

    18. [18]

      Qiuyang LUOXiaoning TANGShu XIAJunnan LIUXingfu YANGJie LEI . Application of a densely hydrophobic copper metal layer in-situ prepared with organic solvents for protecting zinc anodes. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1243-1253. doi: 10.11862/CJIC.20240110

    19. [19]

      Wei Li Jinfan Xu Yongjun Zhang Ying Guan . 共价有机框架整体材料的制备及食品安全非靶向筛查应用——推荐一个仪器分析综合化学实验. University Chemistry, 2025, 40(6): 276-285. doi: 10.12461/PKU.DXHX202406013

    20. [20]

      Wenjie SHIFan LUMengwei CHENJin WANGYingfeng HAN . Synthesis and host-guest properties of imidazolium-functionalized zirconium metal-organic cage. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 105-113. doi: 10.11862/CJIC.20240360

Metrics
  • PDF Downloads(0)
  • Abstract views(1092)
  • HTML views(171)

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