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

Mao Yu ^a ,
Tian Shaixiao ^a ,
Zhang Wei ^b ,
Xu Guangyu ^a,,

a.
a. Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha. 410081;
b.
b. School of Medicine, Hunan Normal University, Changsha. 410013

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.
- vinamidinium salts,
- preparation,
- organic synthesis,
- application
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.
1. [1]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  Xinzhe HUANG , Lihui XU , Yue YANG , Liming WANG , Zhangyong LIU , Zhongjian 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
5. [5]
  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
6. [6]
  Yuanyin Cui , Jinfeng Zhang , Hailiang Chu , Lixian Sun , Kai Dai . Rational Design of Bismuth Based Photocatalysts for Solar Energy Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2405016-. doi: 10.3866/PKU.WHXB202405016
7. [7]
  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
8. [8]
  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
9. [9]
  Laiying Zhang , Yaxian Zhu . Exploring the Silver Family. University Chemistry, 2024, 39(9): 1-4. doi: 10.12461/PKU.DXHX202409015
10. [10]
  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
11. [11]
  Yuanpei ZHANG , Jiahong WANG , Jinming HUANG , Zhi 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
12. [12]
  Qiuyang LUO , Xiaoning TANG , Shu XIA , Junnan LIU , Xingfu YANG , Jie 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
13. [13]
  Wenjie SHI , Fan LU , Mengwei CHEN , Jin WANG , Yingfeng 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
14. [14]
  Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
15. [15]
  Yukun Chang , Haoqin Huang , Baolei Wang . Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment. University Chemistry, 2024, 39(4): 322-328. doi: 10.3866/PKU.DXHX202309095
16. [16]
  Wendian XIE , Yuehua LONG , Jianyang XIE , Liqun XING , Shixiong SHE , Yan YANG , Zhihao HUANG . Preparation and ion separation performance of oligoether chains enriched covalent organic framework membrane. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1528-1536. doi: 10.11862/CJIC.20240050
17. [17]
  Bao Jia , Yunzhe Ke , Shiyue Sun , Dongxue Yu , Ying Liu , Shuaishuai Ding . Innovative Experimental Teaching for the Preparation and Modification of Conductive Organic Polymer Thin Films in Undergraduate Courses. University Chemistry, 2024, 39(10): 271-282. doi: 10.12461/PKU.DXHX202404121
18. [18]
  Ling Zhang , Jing Kang . Turn Waste into Valuable: Preparation of High-Strength Water-Based Adhesives from Polymethylmethacrylate Wastes: a Comprehensive Chemical Experiments. University Chemistry, 2024, 39(2): 221-226. doi: 10.3866/PKU.DXHX202306075
19. [19]
  Fan Wu , Wenchang Tian , Jin Liu , Qiuting Zhang , YanHui Zhong , Zian Lin . Core-Shell Structured Covalent Organic Framework-Coated Silica Microspheres as Mixed-Mode Stationary Phase for High Performance Liquid Chromatography. University Chemistry, 2024, 39(11): 319-326. doi: 10.12461/PKU.DXHX202403031
20. [20]
  Jiapei Zou , Junyang Zhang , Xuming Wu , Cong Wei , Simin Fang , Yuxi Wang . A Comprehensive Experiment Based on Electrocatalytic Nitrate Reduction into Ammonia: Synthesis, Characterization, Performance Exploration, and Applicable Design of Copper-based Catalysts. University Chemistry, 2024, 39(6): 373-382. doi: 10.3866/PKU.DXHX202312081

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(953)
HTML views(143)

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