Citation: Shen Tao, Ouyang Bo, Zhou Shaodong, Qian Chao, Chen Xinzhi. Efficient, Solvent-Free Aminolysis of Monoesters Catalyzed by Sodium[J]. Chinese Journal of Organic Chemistry, ;2019, 39(3): 873-877. doi: 10.6023/cjoc201808006 shu

Efficient, Solvent-Free Aminolysis of Monoesters Catalyzed by Sodium

Shen Tao ^a ,
Ouyang Bo ^a,b ,
Zhou Shaodong ^a ,
Qian Chao ^a,, ,
Chen Xinzhi ^a

a.
Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology, Zhejiang University, Hangzhou 310027
b.
Zhejiang Garden Biochemical High-Tech Co., LTD, Dongyang 322121

Corresponding author: Qian Chao, qianchao@zju.edu.cn
Received Date: 7 August 2018
Revised Date: 28 September 2018
Available Online: 26 March 2018
Fund Project: the National Key Research and Development Program of China 2016YFB0301800Project supported by the National Natural Science Foundation of China (No. 21476194) and the National Key Research and Development Program of China (No. 2016YFB0301800)the National Natural Science Foundation of China 21476194

Figures(3)

An efficient, solvent-free procedure using sodium as catalyst for the aminolysis of monoesters is reported. A detailed comparison of catalysts between sodium and sodium amide was made. It was found that the fresh sodium amide by in-situ synthesis of sodium with ammonia was more active than the indirectly adding sodium amide. As compared to the previously reported approaches, the procedure given in this work is much faster and performed under mild conditions. Furthermore, this procedure is applied successfully for the aminolysis of other monoesters.
- monoester,
- aminolysis,
- sodium,
- sodium amide
1. [1]
  Montalbetti, C. A. G. N.; Falque, V. Tetrahedron 2005, 61, 10827. doi: 10.1016/j.tet.2005.08.031
2. [2]
  董浩, 侯梅芳, 有机化学, 2017, 37, 267.
3. [3]
  (a) Xie, L. Y.; Li, Y. J.; Qu, J.; Duan, Y.; Hu, J.; Liu, K. J.; Cao, Z.; He, W. M. Green Chem. 2017, 19, 5642.
  (b) Xie, L. Y.; Qu, J.; Peng, S.; Liu, K. J.; Wang, Z.; Ding, M. H.; Wang, Y.; Cao, Z.; He, W. M. Green Chem. 2018, 20, 760.
  (c) Tan, J.; Guo, Y.; Zeng, F.; Chen, G.; Xie, L.; He, W. Chin. J. Org. Chem. 2018, 38, 1740(in Chinese).
  (谭家希, 郭也, 曾飞, 陈观荣, 谢龙勇, 何卫民, 有机化学, 2018, 38, 1740.)
  (d) Xie, L. Y.; Peng, S.; Lu, L. H.; Hu, J.; Bao, W. H.; Zeng, F.; Tang, Z.; Xu, X.; He, W. M. ACS Sustainable Chem. Eng. 2018, 6, 7989.
4. [4]
  (a) Zhang, Q.; Wang, X.; Xiao, Q.; Yin, D. Chin. J. Org. Chem. 2017, 37, 954(in Chinese).
  (张青扬, 汪小涧, 肖琼, 尹大力, 有机化学, 2017, 37, 954.)
  (b) Liu, K. J.; Jiang, S.; Lu, L. H.; Tang, L. L.; Tang, S. S.; Tang, H. S.; Tang, Z.; He, W. M.; Xu, X. Green Chem. 2018, 20, 3038.
  (c) Wu, C.; Lu, L. H.; Peng, A. Z.; Jia, G. K.; Peng, C.; Cao, Z.; Tang, Z.; He, W. M.; Xu, X. Green Chem. 2018, 20, 3683.
  (d) Liu, T.; Peng, Y.; Wang, Y.; Yong, J.; Wang, X. Chin. J. Org. Chem. 2018, 38, 969(in Chinese).
  (刘天宝, 彭艳芬, 王雅洁, 雍家远, 汪新, 有机化学, 2018, 38, 969.
5. [5]
  Constable, D. J. C.; Dunn, P. J.; Hayler, J. D.; Humphrey, G. R.; Leazer, J. J. L.; Linderman, R. J.; Lorenz, K.; Manley, J.; Pearlman, B. A.; Wells, A.; Zaks, A.; Zhang, T. Y. Green Chem. 2007, 9, 411. doi: 10.1039/B703488C
6. [6]
  Joullie, M. M.; Lassen, K. M. ARKIVOC 2010, 189.
7. [7]
  Reimann, S.; Danke, V.; Beiner, M.; Binder, W. H. J. Polym. Sci., Part A:Polym. Chem. 2017, 55, 3736. doi: 10.1002/pola.v55.22
8. [8]
  Afon'kin, A. A.; Kostrikin, L. M.; Shumeiko, A. E.; Popov, A. F.; Matveev, A. A.; Matvienko, V. N.; Zabudkin, A. F. Russ. Chem. Bull. 2012, 61, 2149. doi: 10.1007/s11172-012-0302-4
9. [9]
  Baldessari, A.; Mangone, C. P. J. Mol. Catal. B:Enzym. 2001, 11, 335. doi: 10.1016/S1381-1177(00)00018-7
10. [10]
  Sauer, D. R.; Kalvin, D.; Phelan, K. M. Org. Lett. 2003, 5, 4721. doi: 10.1021/ol0358915
11. [11]
  Polshettiwar, V.; Varma, R. S. Tetrahedron Lett. 2008, 49, 2661. doi: 10.1016/j.tetlet.2008.02.009
12. [12]
  Sharghi, H.; Sarvari, M. H. Synth. Commun. 2003, 33, 207. doi: 10.1081/SCC-120015702
13. [13]
  Ganguly, N. C.; Roy, S.; Mondal, P. Tetrahedron Lett. 2012, 53, 1413. doi: 10.1016/j.tetlet.2012.01.029
14. [14]
  Allam, B. K.; Singh, K. N. Tetrahedron Lett. 2011, 52, 5851. doi: 10.1016/j.tetlet.2011.08.150
15. [15]
  Zhang, J.; Leitus, G.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 2005, 127, 12429. doi: 10.1021/ja059914h
16. [16]
  Zhang, J.; Gandelman, M.; Shimon, L. J. W.; Rozenberg, H.; Milstein, D. Organometallics 2004, 23, 4026. doi: 10.1021/om049716j
17. [17]
  Chan, W. K.; Ho, C. M.; Wong, M. K.; Che, C. M. J. Am. Chem. Soc. 2006, 128, 14796. doi: 10.1021/ja064479s
18. [18]
  Hogberg, T.; Strom, P.; Ebner, M.; Ramsby, S. J. Org. Chem. 1987, 52, 2033. doi: 10.1021/jo00386a025
19. [19]
  Arora, R.; Paul, S.; Gupta, R. Can. J. Chem. 2005, 83, 1137. doi: 10.1139/v05-134
20. [20]
  Burkhardt, I.; Lauterbach, L.; Brock, N. L.; Dickschat, J. S. Org. Biomol. Chem. 2017, 15, 4432. doi: 10.1039/C7OB00913E
21. [21]
  Lin, J. J.; Wu, J. J.; Ho, Y. S. J. Appl. Polym. Sci. 2001, 82, 435. doi: 10.1002/(ISSN)1097-4628
22. [22]
  Yang, K. W.; Cannon, J. G.; Rose, J. G. Tetrahedron Lett. 1970, 1791. doi: 10.1016/S0040-4039(01)98084-0
23. [23]
  Xie, L. Y.; Peng, S.; Liu, F.; Chen, G. R.; Xia, W.; Yu, X.; Li, W. F.; Cao, Z.; He, W. M. Org. Chem. Front. 2018, 5, 2604. doi: 10.1039/C8QO00661J
24. [24]
  余晓叶, 周帆, 陈加荣, 肖文精, 化学学报, 2017, 75, 86.
25. [25]
  张俊辉, 牛李智, 李映, 刘思, 姜林, 有机化学, 2018, 38, 1842. doi: 10.6023/cjoc201801019
26. [26]
  Greenlee, K. W.; Henne, A. L. Inorg. Synth. 1946, 2, 128. doi: 10.1021/ja01250a056
27. [27]
  Willard, M. L.; Maresh, C. J. Am. Chem. Soc. 1940, 62, 1253. doi: 10.1021/ja01862a077
28. [28]
  Kuzma, P. C.; Brown, L. E.; Harris, T. M. J. Org. Chem. 1984, 49, 2015. doi: 10.1021/jo00185a038
29. [29]
  Philbrook, G. E. J. Org. Chem. 1954, 19, 623. doi: 10.1021/jo01369a022
30. [30]
  Behun, J. D.; Levine, R. J. Am. Chem. Soc. 1959, 81, 5157. doi: 10.1021/ja01528a034
31. [31]
  Ohmura, R.; Takahata, M.; Togo, H. Tetrahedron Lett. 2010, 51, 4378. doi: 10.1016/j.tetlet.2010.06.051
32. [32]
  Chinchilla, R.; Dodsworth, D. J.; Najera, C.; Soriano, J. M. Tetrahedron Lett. 2003, 44, 463. doi: 10.1016/S0040-4039(02)02592-3
33. [33]
  Ma, X. Y.; Lu, M. J. Chem. Res. 2011, 480. doi: 10.1002/cbdv.201000366
1. [1]
  Yao Wang , Jun Ouyang , Huadong Yuan , Jianmin Luo , Shihui Zou , Jianwei Nai , Xinyong Tao , Yujing Liu . Impact of local amorphous environment on the diffusion of sodium ions at the solid electrolyte interface in sodium-ion batteries. Chinese Chemical Letters, 2025, 36(10): 110412-. doi: 10.1016/j.cclet.2024.110412
2. [2]
  Haiying Lu , Weijie Li . The electrolyte solvation and interfacial chemistry for anode-free sodium metal batteries. Chinese Journal of Structural Chemistry, 2024, 43(11): 100334-100334. doi: 10.1016/j.cjsc.2024.100334
3. [3]
  Zhenyang Yu , Yueyue Gu , Qi Sun , Yang Zheng , Yifang Zhang , Mengmeng Zhang , Delin Zhang , Zhijia Zhang , Yong Jiang . Research progress of modified metal current collectors in sodium metal anodes. Chinese Chemical Letters, 2025, 36(6): 109997-. doi: 10.1016/j.cclet.2024.109997
4. [4]
  Qiao Wang , Ziling Jiang , Chuang Yu , Liping Li , Guangshe Li . Research progress of inorganic sodium ion conductors for solid-state batteries. Chinese Chemical Letters, 2025, 36(6): 110006-. doi: 10.1016/j.cclet.2024.110006
5. [5]
  Shengyu Zhao , Qinhao Shi , Wuliang Feng , Yang Liu , Xinxin Yang , Xingli Zou , Xionggang Lu , Yufeng Zhao . Suppression of multistep phase transitions of O3-type cathode for sodium-ion batteries. Chinese Chemical Letters, 2024, 35(5): 108606-. doi: 10.1016/j.cclet.2023.108606
6. [6]
  Xiping Dong , Xuan Wang , Zhixiu Lu , Qinhao Shi , Zhengyi Yang , Xuan Yu , Wuliang Feng , Xingli Zou , Yang Liu , Yufeng Zhao . Construction of Cu-Zn Co-doped layered materials for sodium-ion batteries with high cycle stability. Chinese Chemical Letters, 2024, 35(5): 108605-. doi: 10.1016/j.cclet.2023.108605
7. [7]
  Fabrice Nelly Habarugira , Ducheng Yao , Wei Miao , Chengcheng Chu , Zhong Chen , Shun Mao . Synergy of sodium doping and nitrogen defects in carbon nitride for promoted photocatalytic synthesis of hydrogen peroxide. Chinese Chemical Letters, 2024, 35(8): 109886-. doi: 10.1016/j.cclet.2024.109886
8. [8]
  Mingxin Song , Lijing Xie , Fangyuan Su , Zonglin Yi , Quangui Guo , Cheng-Meng Chen . New insights into the effect of hard carbons microstructure on the diffusion of sodium ions into closed pores. Chinese Chemical Letters, 2024, 35(6): 109266-. doi: 10.1016/j.cclet.2023.109266
9. [9]
  Zhijia Zhang , Shihao Sun , Yuefang Chen , Yanhao Wei , Mengmeng Zhang , Chunsheng Li , Yan Sun , Shaofei Zhang , Yong Jiang . Epitaxial growth of Cu_2-xSe on Cu (220) crystal plane as high property anode for sodium storage. Chinese Chemical Letters, 2024, 35(7): 108922-. doi: 10.1016/j.cclet.2023.108922
10. [10]
  Jun-Ming Cao , Kai-Yang Zhang , Jia-Lin Yang , Zhen-Yi Gu , Xing-Long Wu . Differential bonding behaviors of sodium/potassium-ion storage in sawdust waste carbon derivatives. Chinese Chemical Letters, 2024, 35(4): 109304-. doi: 10.1016/j.cclet.2023.109304
11. [11]
  Shengyu Zhao , Xuan Yu , Yufeng Zhao . A water-stable high-voltage P3-type cathode for sodium-ion batteries. Chinese Chemical Letters, 2024, 35(9): 109933-. doi: 10.1016/j.cclet.2024.109933
12. [12]
  Changyuan Bao , Yunpeng Jiang , Haoyin Zhong , Huaizheng Ren , Junhui Wang , Binbin Liu , Qi Zhao , Fan Jin , Yan Meng Chong , Jianguo Sun , Fei Wang , Bo Wang , Ximeng Liu , Dianlong Wang , John Wang . Synergizing 3D-printed structure and sodiophilic interface enables highly efficient sodium metal anodes. Chinese Chemical Letters, 2024, 35(11): 109353-. doi: 10.1016/j.cclet.2023.109353
13. [13]
  Fan Wu , Shaoyang Wu , Xin Ye , Yurong Ren , Peng Wei . Research progress of high-entropy cathode materials for sodium-ion batteries. Chinese Chemical Letters, 2025, 36(4): 109851-. doi: 10.1016/j.cclet.2024.109851
14. [14]
  Xuan Wang , Peng Sun , Siteng Yuan , Lu Yue , Yufeng Zhao . P2-type low-cost and moisture-stable cathode for sodium-ion batteries. Chinese Chemical Letters, 2025, 36(5): 110015-. doi: 10.1016/j.cclet.2024.110015
15. [15]
  Run Chai , Qiujie Wu , Yongchao Liu , Xiaohui Song , Xuyong Feng , Yi Sun , Hongfa Xiang . A 3D dual layer host with enhanced sodiophilicity as stable anode for high-energy sodium metal batteries. Chinese Chemical Letters, 2025, 36(6): 110007-. doi: 10.1016/j.cclet.2024.110007
16. [16]
  Yanxue Wu , Xijun Xu , Shanshan Shi , Fangkun Li , Shaomin Ji , Jingwei Zhao , Jun Liu , Yanping Huo . Facile construction of Cu_2-xSe@C nanobelts as anode for superior sodium-ion storage. Chinese Chemical Letters, 2025, 36(6): 110062-. doi: 10.1016/j.cclet.2024.110062
17. [17]
  Guang Zeng , Yue Zeng , Huamin Hu , Yaqing Bai , Fangjie Nie , Junfei Duan , Zhaoyong Chen , Qi-Long Zhu . Regulating pore structure and pseudo-graphitic phase of hard carbon anode towards enhanced sodium storage performance. Chinese Chemical Letters, 2025, 36(7): 110122-. doi: 10.1016/j.cclet.2024.110122
18. [18]
  Liangju Zhao , Shiyu Qin , Fei Wu , Limin Zhu , Qing Han , Lingling Xie , Xuejing Qiu , Hongliang Wei , Lanhua Yi , Xiaoyu Cao . Polycarbonyl conjugated porous polyimide as anode materials for high performance sodium-ion batteries. Chinese Chemical Letters, 2025, 36(8): 110246-. doi: 10.1016/j.cclet.2024.110246
19. [19]
  Huifang Ma , Tao Xu , Saifei Yuan , Shujuan Li , Jiayao Wang , Yuping Zhang , Hao Ren , Shulai Lei . Interlayer interactions and electron transfer effects on sodium adsorption on 2D heterostructures surfaces. Chinese Chemical Letters, 2025, 36(8): 110219-. doi: 10.1016/j.cclet.2024.110219
20. [20]
  Binyang Qin , Mengqi Wang , Shimei Wu , Yining Li , Chilin Liu , Yufei Zhang , Haosen Fan . Carbon dots confined nanosheets assembled NiCo₂S₄@CDs cross-stacked architecture for enhanced sodium ion storage. Chinese Chemical Letters, 2024, 35(7): 108921-. doi: 10.1016/j.cclet.2023.108921

Get Citation

PDF

XML

Metrics

PDF Downloads(11)
Abstract views(1861)
HTML views(154)

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