Citation: Maorong Wang, Bao Gao, Hanmin Huang. Catalytic nucleophilic addition of terminal alkynes to α,β-unsaturated-γ-lactams[J]. Chinese Journal of Catalysis, ;2016, 37(4): 476-483. doi: 10.1016/S1872-2067(15)61057-9 shu

Catalytic nucleophilic addition of terminal alkynes to α,β-unsaturated-γ-lactams

Maorong Wang ^a,b ,
Bao Gao ^a,b ,
Hanmin Huang ^a,,

a.
a State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, Gansu, China;
b.
b University of Chinese Academy of Sciences, Beijing 100049, China

Corresponding author: Hanmin Huang,
Received Date: 11 January 2016
Available Online: 26 January 2016
Fund Project: 国家自然科学基金(21222203, 21172226, 21133011). (21222203, 21172226, 21133011)

A novel catalytic reaction has been developed for the nucleophilic addition of terminal alkynes to α,β-unsaturated-γ-lactams via a cyclic N-acyliminium ion intermediate. This simple reaction proceeds rapidly under mild conditions, and provided a practical approach for the synthesis of a wide range of 5-alkynyl-2-pyrrolidinones in moderate to good yields (45%-76%).
- Carbon-hydrogen addition,
- Brönsted acid,
- N-Acyliminium ion,
- Terminal alkyne,
- Pyrrolidin-2-one
1. [1]
  [1] T. Harrison, Contemp. Org. Synth., 1995, 2, 209-224.
2. [2]
  [2] Y. R. Lee, J. Y. Suk, B. S. Kim, Tetrahedron Lett., 1999, 40, 8219-8221.
3. [3]
  [3] K. L. Vine, J. M. Locke, M. Ranson, S. G. Pyne, J. B. Bremner, J. Med. Chem., 2007, 50, 5109-5117.
4. [4]
  [4] T. Trellenkamp, H. Ritter, Macromolecules, 2010, 43, 5538-5543.
5. [5]
  [5] T. Suzuki, R. Tanaka, S. Hamada, H. Nakagawa, N. Miyata, Bioorg. Med. Chem. Lett., 2010, 20, 1124-1127.
6. [6]
  [6] D. W. Old, US Patent 20080015239, 2008.
7. [7]
  [7] A. Enz, D. Feuerbach, M. U. Frederiksen, C. Gentsch, K. Hurth, W. Müller, J. Nozulak, B. L. Roy, Bioorg. Med. Chem. Lett., 2009, 19, 1287-1291.
8. [8]
  [8] B. E. Torian, L. L. Braun, J. Heterocycl. Chem., 1984, 21, 293-295.
9. [9]
  [9] Z. Kałuża, D. Mostowicz, G. Dołęga, R. Wójcik, Tetrahedron, 2008, 64, 2321-2328.
10. [10]
  [10] T. Bootwicha, D. Panichakul, C. Kuhakarn, S. Prabpai, P. Kongsaeree, P. Tuchinda, V. Reutrakul, M. Pohmakotr, J. Org. Chem., 2009, 74, 3798-3805.
11. [11]
  [11] S. Mori, H. Iwakura, S. Takechi, Tetrahedron Lett., 1988, 29, 5391-5394.
12. [12]
  [12] P. A. Jacobi, K. Lee, J. Am. Chem. Soc., 2000, 122, 4295-4303.
13. [13]
  [13] A. R. Katritzky, S. Mehta, H. Y. He, X. L. Cui, J. Org. Chem., 2000, 65, 4364-4369.
14. [14]
  [14] R. A. Pilli, L. G. Robello, Synlett, 2005, 2297-2300.
15. [15]
  [15] J. H. Zhang, C. M. Wei, C. J. Li, Tetrahedron Lett., 2002, 43, 5731-5733.
16. [16]
  [16] B. Qian, S. M. Guo, J. P. Shao, Q. M. Zhu, L. Yang, C. G. Xia, H. M. Huang, J. Am. Chem. Soc., 2010, 132, 3650-3651.
17. [17]
  [17] B. Qian, S. M. Guo, C. G. Xia, H. M. Huang, Adv. Synth. Catal., 2010, 352, 3195-3200.
18. [18]
  [18] B. Qian, D. J. Shi, L. Yang, H. M. Huang, Adv. Synth. Catal., 2012, 354, 2146-2150.
19. [19]
  [19] B. Qian, G. Y. Zhang, Y. Z. Ding, H. M. Huang, Chem. Commun., 2013, 49, 9839-9841.
20. [20]
  [20] B. Qian, L. Yang, H. M. Huang, Tetrahedron Lett., 2013, 54, 711-714.
21. [21]
  [21] B. Qian, C. F. Qiao, Y. J. Xie, H. M. Huang, ChemCatChem, 2015, 7, 250-253.
22. [22]
  [22] L. Yang, H. M. Huang, Chem. Rev., 2015, 115, 3468-3517.
23. [23]
  [23] M. R. Wang, B. Gao, H. M. Huang, Tetrahedron Lett., 2015, 56, 5533-5536.
24. [24]
  [24] M. M. Sun, H. D. Wu, W. L. Bao, Org. Biomol. Chem., 2013, 11, 7076-7079.
25. [25]
  [25] S. Peixoto, T. M. Nguyen, D. Crich, B. Delpech, C. Marazano, Org. Lett., 2010, 12, 4760-4763.
26. [26]
  [26] E. Aranzamendi, N. Sotomayor, E. Lete, J. Org. Chem., 2012, 77, 2986-2991.
27. [27]
  [27] Y. S. Lee, M. M. Alam, R. S. Keri, Chem. Asian. J., 2013, 8, 2906-2919.
28. [28]
  [28] S. Gunawan, C. Hulme, Tetrahedron Lett., 2013, 54, 4467-4470.
29. [29]
  [29] J. Royer, M. Bonin, L. Micouin, Chem. Rev., 2004, 104, 2311-2352.
30. [30]
  [30] I. T. Raheem, P. S. Thiara, E. A. Peterson, E. N. Jacobsen, J. Am. Chem. Soc., 2007, 129, 13404-13405.
31. [31]
  [31] E. A. Peterson, E. N. Jacobsen, Angew. Chem. Int. Ed., 2009, 48, 6328-6331.
32. [32]
  [32] M. E. Muratore, C. A. Holloway, A. W. Pilling, R. I. Storer, G. Trevitt, D. J. Dixon, J. Am. Chem. Soc., 2009, 131, 10796-10797.
33. [33]
  [33] Y. J. Xie, Y. W. Zhao, B. Qian, L. Yang, C. G. Xia, H. M. Huang, Angew. Chem. Int. Ed., 2011, 50, 5682-5686.
34. [34]
  [34] W. L. F. Armarego, Purification of Laboratory Chemicals, 4th Ed., Elsevier, Amsterdam, 1997.
35. [35]
  [35] I. Baussanne, J. Royer, Tetrahedron Lett., 1996, 37, 1213-1216.
36. [36]
  [36] I. Baussanne, J. Royer, Tetrahedron Lett., 1998, 39, 845-848.
37. [37]
  [37] L. Planas, J. Perard-Viret, J. Royer, M. Selkti, A. Thomas, Synlett, 2002, 1629-1632.
38. [38]
  [38] E. J. Corey, P. L. Fuchs, Tetrahedron Lett., 1972, 13, 3769-3772.
39. [39]
  [39] N. B. Desai, N. McKelvie, F. Ramirez, J. Am. Chem. Soc., 1962, 84, 1745-1747.
40. [40]
  [40] J. Uenishi, T. Iwamoto, M. Ohmi, Tetrahedron Lett., 2007, 48, 1237-1240.
41. [41]
  [41] V. Bocchi, L. Chierici, G. P. Gardini, R. Mondelli, Tetrahedron, 1970, 26, 4073-4082.
42. [42]
  [42] I. Baussanne, A. Chiaroni, H. P. Husson, C. Riche, J. Royer, Tetrahedron Lett., 1994, 35, 3931-3934.
43. [43]
  [43] Y. H. Ma, S. Zhang, S. P. Yang, F. J. Song, J. S. You, Angew. Chem. Int. Ed., 2014, 53, 7870-7874.
44. [44]
  [44] M. N. Hopkinson, J. E. Ross, G. T. Giuffredi, A. D. Gee, V. Gouverneur, Org. Lett., 2010, 12, 4904-4907.
45. [45]
  [45] T. de Haro, C. Nevado, J. Am. Chem. Soc., 2010, 132, 1512-1513.
1. [1]
  Lirui Shen , Kun Liu , Ying Yang , Dongwan Li , Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035
2. [2]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
3. [3]
  Yujie WANG , Laobang WANG , Zheng ZHANG , Qi LIU , Jianping LANG . Construction of W/Cu/S cluster-based supramolecular compounds via alkynyl/sulfur cycloaddition and their third-order nonlinear optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2069-2077. doi: 10.11862/CJIC.20250129
4. [4]
  Zhengyu Zhou , Huiqin Yao , Youlin Wu , Teng Li , Noritatsu Tsubaki , Zhiliang Jin . Synergistic Effect of Cu-Graphdiyne/Transition Bimetallic Tungstate Formed S-Scheme Heterojunction for Enhanced Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(10): 2312010-0. doi: 10.3866/PKU.WHXB202312010
5. [5]
  Caixia Lin , Ting Liu , Zhaojiang Shi , Hong Yan , Keyin Ye , Yaofeng Yuan . Innovative Experiment of Electrochemical Dearomative Spirocyclization of N-Acyl Sulfonamides. University Chemistry, 2025, 40(4): 359-366. doi: 10.12461/PKU.DXHX202406107
6. [6]
  Xiaofeng Xia , Jielian Zhu . Innovative Comprehensive Experimental Design: Synthesis of 6-Fluoro-N-benzoyl Tetrahydroquinoline. University Chemistry, 2024, 39(10): 344-352. doi: 10.12461/PKU.DXHX202405063
7. [7]
  Zhanhui Yang , Jiaxi Xu . (m+n+…) or [m+n+…]cycloaddition?. University Chemistry, 2025, 40(3): 387-389. doi: 10.12461/PKU.DXHX202406032
8. [8]
  Huirong BAO , Jun YANG , Xiaomiao FENG . Preparation and electrochemical properties of NiCoP/polypyrrole/carbon cloth by electrodeposition. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1083-1093. doi: 10.11862/CJIC.20250008
9. [9]
  Jiajun Lu , Zhehui Liao , Tongxiang Cao , Shifa Zhu . Synergistic Brønsted/Lewis acid catalyzed atroposelective synthesis of aryl-β-naphthol. Chinese Chemical Letters, 2025, 36(1): 109842-. doi: 10.1016/j.cclet.2024.109842
10. [10]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
11. [11]
  Jiatong Hu , Qiyi Wang , Ruiwen Tang , Jiajing Feng . Photocatalytic Journey of Perylene Diimides in a Competitive Arena. University Chemistry, 2025, 40(5): 328-333. doi: 10.12461/PKU.DXHX202407015
12. [12]
  Xudong Liu , Huili Fan , Junping Xiao , Min Yang , Yan Li . Teaching Approaches to the A_E + A_N Mechanism of Electrophilic Addition Reactions between Olefins and Inorganic Acids in Organic Chemistry. University Chemistry, 2025, 40(7): 367-372. doi: 10.12461/PKU.DXHX202409041
13. [13]
  Runze Liu , Yankai Bian , Weili Dai . Qualitative and quantitative analysis of Brønsted and Lewis acid sites in zeolites: A combined probe-assisted 1H MAS NMR and NH3-TPD investigation. Chinese Journal of Structural Chemistry, 2024, 43(4): 100250-100250. doi: 10.1016/j.cjsc.2024.100250
14. [14]
  Kai CHEN , Fengshun WU , Shun XIAO , Jinbao ZHANG , Lihua ZHU . PtRu/nitrogen-doped carbon for electrocatalytic methanol oxidation and hydrogen evolution by water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1357-1367. doi: 10.11862/CJIC.20230350
15. [15]
  Yongwei ZHANG , Chuang ZHU , Wenbin WU , Yongyong MA , Heng YANG . Efficient hydrogen evolution reaction activity induced by ZnSe@nitrogen doped porous carbon heterojunction. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 650-660. doi: 10.11862/CJIC.20240386
16. [16]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . Research Progress on Carbon-based Catalysts for Catalytic Dehydrogenation of Liquid Organic Hydrogen Carriers. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-0. doi: 10.1016/j.actphy.2024.100044
17. [17]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
18. [18]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
19. [19]
  Ran Yu , Chen Hu , Ruili Guo , Ruonan Liu , Lixing Xia , Cenyu Yang , Jianglan Shui . Catalytic Effect of H₃PW₁₂O₄₀ on Hydrogen Storage of MgH₂. Acta Physico-Chimica Sinica, 2025, 41(1): 100001-0. doi: 10.3866/PKU.WHXB202308032
20. [20]
  Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(692)
HTML views(67)

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