Citation: Li Xuedong, Lang Xiandong, Song Qingwen, Guo Yakun, He Liangnian. Cu(I)-Catalyzed Three-Component Reaction of Propargylic Alcohol, Secondary Amines and Atmospheric CO₂[J]. Chinese Journal of Organic Chemistry, ;2016, 36(4): 744-751. doi: 10.6023/cjoc201512037 shu

Cu(I)-Catalyzed Three-Component Reaction of Propargylic Alcohol, Secondary Amines and Atmospheric CO₂

1.
State Key Laboratory and Institute of Elemento-Organic. Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071

Corresponding author: He Liangnian,
Received Date: 25 December 2015
Available Online: 30 January 2016
Fund Project: 国家自然科学基金(Nos.21472103,21121002) (Nos.21472103,21121002)教育部博士点基金(No.20130031110013) (No.20130031110013)国家基础科学人才培养基金(No.J1103306)资助项目. (No.J1103306)

β-Oxopropylcarbamates constitute an important kind of organic compounds, owing to the extensive applications in agrochemicals, pharmaceuticals, organic synthesis, and protection of amino group. In this article, an efficient and atom-economical Cu(I) catalyzed three-component reaction of propargylic alcohols, secondary amines and CO₂ has been developed under atmospheric pressure, affording various β-oxopropylcarbamates in high yields with high selectivity by controlling the concentration of O₂. This protocol avoids the use of high pressure of CO₂ and provides an extremely simple way to access the synthetically useful β-oxopropylcarbamates.
- CO₂,
- homogeneous catalysis,
- synthetic methods,
- Cu,
- three-component reaction,
- β-oxopropylcarbamates
1. [1]
  [1] (a) He, L.-N. CO₂ Chemistry, Science Press, Beijing, 2013 (in Chinese). (何良年, 二氧化碳化学, 科学出版社, 北京, 2013.)
2. [2]
  (b) Otto, A.; Grube, T.; Schiebahna, S.; Stolten, D. Energy Environ. Sci. 2015, 8, 3283.
3. [3]
  [2] Li, J. H.; Jia, L. Q.; Jiang, H. F. Chin. J. Org. Chem. 2000, 20, 293 (in Chinese). (李金恒, 贾兰齐, 江焕峰, 有机化学, 2000, 20, 293.)
4. [4]
  [3] (a) Sakakura, T.; Choi, J.; Yasuda, H. Chem. Rev. 2007, 107, 2365.
5. [5]
  (b) Gao, J.; Miao, C.; Wang, J.; He, L.-N. Petrochemical Technol. 2010, 39, 465 (in Chinese). (高健, 苗成霞, 汪靖伦, 何良年, 石油化工, 2010, 39, 465.)
6. [6]
  (c) Ji, D. F.; Lu, X. B.; He, R.; Zhan, X. L.; Yang, Y. R. Chem. J. Chin. Univ. 2001, 22, 1720 (in Chinese). (季东锋, 吕小兵, 何仁, 詹晓力, 阳永荣, 高等学校化学学报, 2001, 22, 1720.)
7. [7]
  [4] For trepresentative reviews and reports on carbon capture and utilization, see: (a) Li, Y. N.; Ma, R.; He, L.-N.; Diao, Z. F. Catal. Sci. Technol. 2014, 4, 1498.
8. [8]
  (b) Li, Y. N.; He, L.-N. Chin. Sci.Bull. 2015, 60, 1465 (in Chinese). (李雨浓, 何良年, 科学通报, 2015, 60, 1465.)
9. [9]
  (c) Yang, Z. Z.; Zhao, Y. N.; He, L.-N. RSC Adv. 2011, 1, 545.
10. [10]
  (d) Yang, Z. Z.; He, L.-N.; Zhao, Y. N.; Li, B.; Yu, B. Energy Environ. Sci. 2011, 4, 3971.
11. [11]
  (e) Liu, A. H.; Ma, R.; Song, C.; Yang, Z. Z.; Yu, A.; Cai, Y.; He, L.-N.; Zhao, Y. N.; Yu, B.; Song, Q. W. Angew. Chem., Int. Ed. 2012, 51, 11306.
12. [12]
  (f) Zhang, S.; Li, Y. N.; Zhang, Y. W.; He, L.-N.; Yu, B.; Song, Q. W.; Lang, X. D. ChemSusChem. 2014, 7, 1484.
13. [13]
  [5] (a) He, M.; Sun, Y.; Han, B. Angew. Chem., Int. Ed. 2013, 52, 9620.
14. [14]
  (b) He, M.; Sun, Y.; Han, B. Chin. Sci. Bull. 2015, 60, 1421 (in Chinese). (何鸣元, 孙予罕, 韩布兴, 科学通报, 2015, 60, 1421.)
15. [15]
  [6] Wu, T. T.; Huang, J.; Arrington, N. D.; Dill, G. M. J. Agric. Food Chem. 1987, 35, 817.
16. [16]
  [7] Vauthey, I.; Valot, F.; Gozzi, C.; Fache, F.; Lemaire, M. Tetrahedron Lett. 2000, 41, 6347.
17. [17]
  [8] McGhee, W. D.; Pan, Y.; Riley, D. P. J. Chem. Soc., Chem. Commun. 1994, 6, 699.
18. [18]
  [9] McGhee, W.; Riley, D.; Christ, K.; Pan, Y.; Parnas, B. J. Org. Chem. 1995, 60, 2820.
19. [19]
  [10] Salvatore, R. N.; Shin, S.; Nagle, A. S.; Jung, K. W. J. Org. Chem. 2001, 66, 1035.
20. [20]
  [11] Yoshida, M.; Hara, N.; Okuyama, S. Chem. Commun. 2000, 151.
21. [21]
  [12] Srivastava, R.; Srinivas, D.; Ratnasamy, P. Appl. Catal. A: Gen. 2005, 289, 128.
22. [22]
  [13] Kong, D. L.; He, L. N.; Wang, J. Q. Synth. Commun. 2011, 41, 3298.
23. [23]
  [14] Ion, A.; Van Doorslaer, C.; Parvulescu, V.; Jacobs, P.; De Vos, D. Green Chem. 2008, 10, 111.
24. [24]
  [15] Chaturvedi, D.; Kumar, A.; Ray, S. Tetrahedron Lett. 2003, 44, 7637.
25. [25]
  [16] Abla, M.; Choi, J. C.; Sakakura, T. Chem. Commun. 2001, 2238.
26. [26]
  [17] Mahe, R.; Sasaki, Y.; Bruneau, C.; Dixneuf, P. H. J. Org. Chem. 1989, 54, 1518.
27. [27]
  [18] Selva, M.; Tundo, P.; Perosa, A. Tetrahedron Lett. 2002, 43, 1217.
28. [28]
  [19] Dell'Amico, D. B.; Calderazzo, F.; Labella, L.; Marchetti, F.; Pampaloni, G. Chem. Rev. 2003, 103, 3857.
29. [29]
  [20] Yang, Z. Z.; He, L. N.; Gao, J.; Liu, A. H.; Yu, B. Energy Environ. Sci. 2012, 5, 6602.
30. [30]
  [21] Della, C. N.; Gabriele, B.; Ruffolo, G.; Veltri, L.; Zanetta, T.; Costa, M. Adv. Synth. Catal. 2011, 353, 133.
31. [31]
  [22] Qi, C. R.; Jiang, H. F. Green Chem. 2007, 9. 1284.
32. [32]
  [23] Sasaki, Y.; Dixncuf, P. H. J. Org. Chem. 1987, 52, 4389.
33. [33]
  [24] Bruncau, C.; Dixncuf, P. H.; Tetrahedron Lett. 1987, 28, 2005.
34. [34]
  [25] Qi, C. R.; Huang, L. B.; Jiang, H. F. Synthesis 2010, 1433.
35. [35]
  [26] Kim, H. S.; Kim, J. W.; Kwon, S. C.; Shim, S. C.; Kim, T. J. J. Organomet. Chem. 1997, 545~546, 337.
36. [36]
  [27] Kim, T. J.; Kwon, K. H.; Kwon, S. C.; Baeg, J. O.; Shim, S. C.; Lee, D. H. J. Organomet. Chem. 1990, 389, 205.
37. [37]
  [28] Song, Q. W.; Yu, B.; Li, X. D.; Ma, R.; Diao, Z. F.; Li, R. G.; Li, W.; He, L. N. Green Chem. 2014, 16, 1633.
38. [38]
  [29] Song, Q. W.; Chen, W. Q.; Ma, R.; Yu, A.; Li, Q. Y.; Chang, Y.; He, L. N. ChemSusChem 2015, 8, 821.
39. [39]
  [30] Jiang, H. F.; Zhao, J. W.; Wang, A. Z. Synthesis 2008, 763.
40. [40]
  [31] Pinaka, A.; Vougioukalakis, G. C. Coord. Chem. Rev. 2015, 288, 69.
41. [41]
  [32] (a) Li, Y. N.; Wang, J. N.; He, L.-N. Tetrahedron Lett. 2011, 52, 3485.
42. [42]
  (b) Yang, Z.; Wang, B.; Xu, X.; Wang, H.; Li, X. Chin. J. Org. Chem. 2015, 35, 207 (in Chinese). (杨振平, 王兵南, 许孝良, 王红, 李小年, 有机化学, 2015, 35, 207.)
43. [43]
  [33] Hu, J.; Ma, J.; Zhu, Q.; Qian, Q.; Han, H.; Mei, Q.; Han, B. Green Chem. 2016, 18, 382.
44. [44]
  [34] Gu, Y. L.; Shi, F.; Deng, Y. Q. J. Org. Chem. 2004, 69, 391.
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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

Cu(I)-Catalyzed Three-Component Reaction of Propargylic Alcohol, Secondary Amines and Atmospheric CO2

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通讯作者: 陈斌, bchen63@163.com

Cu(I)-Catalyzed Three-Component Reaction of Propargylic Alcohol, Secondary Amines and Atmospheric CO₂