Citation: Wang Lili, Li Pengshuai, Jia Meilin, Bao Yongsheng. Aminolysis of Esters Using Quaternary Ammonium Salts as Amine Sources via Twice C-N Bond Activations[J]. Chinese Journal of Organic Chemistry, ;2017, 37(5): 1220-1230. doi: 10.6023/cjoc201612014 shu

Aminolysis of Esters Using Quaternary Ammonium Salts as Amine Sources via Twice C-N Bond Activations

Inner Mongolia Key Laboratory of Green Catalysis, College of Chemistry and Environmental Science, Inner Mongolia Normal University, Hohhot 010022

Corresponding author: Bao Yongsheng, sbbys197812@163.com
Received Date: 6 December 2016
Revised Date: 13 February 2017

Fund Project: the Research Program of Science and Technology at University of Inner Mongolia Autonomous Region NJZZ14032the Initial Special Research for National Basic Research Program of China 2014CB460609by the National Natural Science Foundation of China 21462031

Figures(6)

Catalyzed by supported palladium nanoparticles, an aminolysis reaction between various aryl esters and quaternary ammonium salts via twice C-N bond activations has been developed for selectively synthesis of amides. The Pd/γ-Al₂O₃ catalyst exhibited an excellent catalytic activity and reusability of at least five recycles in air for the reaction. The experiment results indicated that the first C-N cleavage of quaternary ammonium salt affords the tertiary amine and halohydrocarbon, and the second C-N cleavage proceeds via the formation of an iminium intermediate.
- quaternary ammonium salts,
- aminolysis,
- palladium,
- C-N activation,
- aryl esters
1. [1]
  (a) Pattabiraman, V. R. ; Bode, J. W. Nature 2011, 480, 471. (b) Allen, C. L. ; Williams, J. M. J. Chem. Soc. Rev. 2011, 40, 3405. (c) Valeur, E. ; Bradley, M. Chem. Soc. Rev. 2009, 38, 606.
2. [2]
  Bai, C. H.; Yao, X. F.; Li, Y. W. ACS Catal. 2015, 5, 884. doi: 10.1021/cs501822r
3. [3]
  (a) Nekkanti, S. ; Veeramani, K. ; Kumar, N. P. ; Shankaraiah, N. Green chem. 2016, 18, 3439. (b) Wu, K. ; Huang, Z. L. ; Ma, Y. Y. ; Lei, A. W. RSC Adv. 2016, 6, 24349.
4. [4]
  Arefi, M.; Saberi, D.; Karimi, M.; Heydari, A. ACS Comb. Sci. 2015, 17, 341. doi: 10.1021/co5001844
5. [5]
  Ouyang, K.; Hao, W.; Zhang, W. X.; Xi, Z. Chem. Rev. 2015, 115, 12045. doi: 10.1021/acs.chemrev.5b00386
6. [6]
  (a) Bao, Y. S. ; Baiyin, M. ; Agula, B. ; Jia, M. L. ; Bao, Z. J. Org. Chem. 2014, 79, 6715. (b) Bao, Y. S. ; Bao, Z. ; Agula, B. ; Baiyin, M. ; Jia, M. L. J. Org. Chem. 2014, 79, 803.
7. [7]
  (a) Li, Y. M. ; Jia, F. ; Li, Z. P. Chem. -Eur. J. 2012, 18, 5150. (b) Porcheddu, A. ; Luca, L. D. Adv. Synth. Catal. 2012, 354, 2949.
8. [8]
  Xu, K.; Hu, Y. B.; Zhang, S.; Zha, Z. G.; Wang, Z. Y. Chem.-Eur. J. 2012, 18, 9793. doi: 10.1002/chem.v18.32
9. [9]
  Du, B.; Sun, P. Sci. China Chem. 2014, 57, 1176.
10. [10]
  Gao, L.; Tang, H.; Wang, Z. Chem. Commun. 2014, 50, 4085. doi: 10.1039/c4cc00621f
11. [11]
  (a) Cassar, L. ; Foa, M. ; Gardano, A. J. Organomet. Chem. 1976, 121, C55. (b) Bhardwaj, M. ; Sahi, S. ; Mahajan, H. ; Paul, S. ; Clark, J. H. J. Mol. Catal. A: Chem. 2015, 408, 48. (c) Zhang, J. T. ; Li, D. Y. ; Chen, H. ; Wang, B. J. ; Liu, Z. X. ; Zhang, Y. H. Adv. Synth. Catal. 2016, 358, 792.
12. [12]
  (a) Wang, X. ; Zhu, L. Z. ; Chen, S. H. ; Xu, X. H. ; Au, C. T. ; Qiu, R. Org. Lett. 2015, 17, 5228. (b) Lin, C. L. ; Li, D. ; Wang, Y. B. ; Yao, J. Z. ; Zhang, Y. H. Org. Lett. 2015, 17, 1328. (c) Fabrizi, G. ; Goggiamani, A. ; Sferrazza, A. ; Cacchi, S. Angew. Chem. , Int. Ed. 2010, 49, 4067. (d) Thirupathi, N. ; Puri, S. ; Reddy, T. J. ; Sridhar, B. ; Reddya, M. S. Adv. Synth. Catal. 2016, 358, 303. (e) Xu, P. ; Han, F. S. ; Wang, Y. H. Adv. Synth. Catal. 2015, 357, 3441. (f) Gadge, S. T. ; Khedkar, M. V. ; Lanke, S. R. ; Bhanage, B. M. Adv. Synth. Catal. 2012, 354, 2049.
13. [13]
  (a) Kim, H. J. ; Kim, J. ; Cho, S. H. ; Chang, S. J. Am. Chem. Soc. 2011, 133, 16382. (b) Xue, Q. C. ; Xie, J. ; Li, H. M. ; Cheng, Y. X. ; Zhu, C. J. Chem. Commun. 2013, 49, 3700. (c) Zhao, D. ; Wang, T. ; Shen, Q. ; Li, J. X. Chem. Commun. 2014, 50, 4302. (d) Wei, W. ; Zhang, C. ; Xu, Y. ; Wan, X. B. Chem. Commun. 2011, 47, 10827. (e) Liu, L. H. ; Yun, L. ; Wang, Z. K. ; Fu, X. F. ; Yan, C. H. Tetrahedron Lett. 2013, 54, 5383. (f) Li, D. J. ; Yang, T. H. ; Su, H. L. ; Yu, W. Adv. Synth. Catal. 2015, 357, 2529. (g) Hao, W. J. ; Du, Y. ; Wang, D. ; Jiang, B. ; Gao, Q. ; Tu, S. J. ; Li, G. G. Org. Lett. 2016, 18, 1884. (h) Zhang, H. ; Dong, D. Q. ; Hao, S. H. ; Wang, Z. L. RSC Adv. 2016, 6, 8465. (i) Tan, B. ; Toda, N. ; Barbas, C. F. Angew. Chem. , Int. Ed. 2012, 51, 12538. (j) Sun, J. W. ; Wang, Y. ; Pan, Y. J. Org. Chem. 2015, 80, 8945. (k) Liu, Z. ; Zhang, J. ; Chen, S. ; Shi, E. ; Xu, Y. ; Wan, X. Angew. Chem. , Int. Ed. 2012, 51, 3231. (l) Uyanik, M. ; Okamoto, H. ; Yasui, T. ; Ishihara, K. Science 2010, 328, 1376.
14. [14]
  (a) Hirao, T. ; Yamada, N. ; Ohshiro, Y. ; Agawa, T. J. Organomet. Chem. 1982, 236, 409. (b) Hosomi, A. ; Hoashi, K. ; Kohra, S. ; Tominaga, Y. ; Otaka, K. ; Sakurai, H. J. Chem. Soc. , Chem. Commun. 1987, 570.
15. [15]
  (a) Wenkert, E. ; Han, A. -L. ; Jenny, C. -J. J. Chem. Soc. , Chem. Commun. 1988, 975. (b) Reeves, J. T. ; Fandrick, D. R. ; Tan, Z. ; Song, J. J. ; Lee, H. ; Yee, N. K. ; Senanayake, C. H. Org. Lett. 2010, 12, 4388.
16. [16]
  Blakey, S. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 6046. doi: 10.1021/ja034908b
17. [17]
  (a) Xie, L. -G. ; Wang, Z. -X. Angew. Chem. , Int. Ed. 2011, 50, 4901. (b) Zhang, X. -Q. ; Wang, Z. -X. J. Org. Chem. 2012, 77, 3658.
18. [18]
  Zhang, X. Q.; Wang, Z.-X. Org. Biomol. Chem. 2014, 12, 1448. doi: 10.1039/c3ob41989d
19. [19]
  (a) Lei, Y. ; Zhang, R. ; Wu, L. ; Wu, Q. ; Mei, H. ; Li, G. Appl. Organomet. Chem. 2014, 28, 310. (b) Lei, Y. ; Zhang, R. ; Wu, Q. ; Mei, H. ; Xiao, B. ; Li, G. J. Mol. Catal. A: Chem. 2014, 381, 120.
20. [20]
  Rozita, Y.; Brydson, R.; Comyn, T. P.; Scott, A. J.; Hammond, C.; Brown, A.; Chauruka, S.; Hassanpour, A.; Young, N. P.; Kirkland, A. I. ChemCatChem 2013, 5, 2695. doi: 10.1002/cctc.v5.9
21. [21]
  Halima, T. B.; Zhang, W.; Yalaoui, I.; Hong, X.; Yang, Y.; Houk, K. N.; Newman, S. G. J. Am. Chem. Soc. 2017, 139, 1311. doi: 10.1021/jacs.6b12329
22. [22]
  Sun, J. W.; Fu, Y. S.; He, G. Y.; Sun, X. Q.; Wang, X. Catal. Sci. Technol. 2014, 4, 1742. doi: 10.1039/c4cy00048j
23. [23]
  Pillo, T.; Zimmermann, R.; Steiner, P.; Hüfner, S. J. Phys.: Condens. Matter 1997, 9, 3987. doi: 10.1088/0953-8984/9/19/018
24. [24]
  Murata, S.; Miura, M.; Nomura, M. J. Org. Chem. 1989, 54, 4700. doi: 10.1021/jo00280a049
25. [25]
  (a) North, M. Angew. Chem. , Int. Ed. 2004, 43, 4126. (b) Murahashi, S. I. ; Komiya, N. ; Terai, H. ; Nakae, T. J. Am. Chem. Soc. 2003, 125, 15312. (c) Murahashi, S. I. ; Komiya, N. ; Terai, H. Angew. Chem. , Int. Ed. 2005, 44, 6931.
26. [26]
  Guo, S. M.; Qian, B.; Xie, Y. J.; Xia, C. G.; Huang, H. M. Org. Lett. 2011, 13, 522. doi: 10.1021/ol1030298
27. [27]
  Zhang, D. L.; Bao, Z.; Bao, Y. S. J. Phys. Chem. C 2015, 119, 20426. doi: 10.1021/acs.jpcc.5b04735
28. [28]
  Naumov, Y. A.; Dremova, V. P.; Kost, A. N.; Mentus, A. N.; Smirnova, S. N. Tr. Vses. Nauch.-Issled. Inst. Dezinfek. Steriliz. 1970, 2, 24.
29. [29]
  Houghton, R. P.; Williams, C. S. Tetrahedron Lett. 1967, 40, 3929.
30. [30]
  Kushner, S.; Dalalian, H.; Sanjurjo, J. L.; BachJr, F. L.; Safir, S. R.; SmithJr, V. K.; Williams, J. H. J. Am. Chem. Soc. 1952, 74, 3617. doi: 10.1021/ja01134a045
31. [31]
  Chow, C. T.; Chi, J. Y. Acta Chim. Sinica 1962, 28, 236 (in Chinese).
32. [32]
  Wu, K.; Huang, Z. L.; Ma, Y. Y.; Lei, A. W. RSC Adv. 2016, 6, 24349. doi: 10.1039/C6RA02153K
33. [33]
  Pathak, U.; Bhattacharyya, S.; Pandey, L. K.; Mathur, S.; Jain, R. RSC Adv. 2014, 4, 3900. doi: 10.1039/C3RA45781H
34. [34]
  Fang, T.; Gao, X. H.; Tang, R. Y.; Zhang, X. G.; Deng, C. L. Chem. Commun. 2014, 50, 14775. doi: 10.1039/C4CC07378A
35. [35]
  Bao, Y. S.; Bao, A.; Bao, Z.; Bai, Y.; Jia, M. J. Org. Chem. 2014, 79, 803. doi: 10.1021/jo4023974
36. [36]
  Bhattacharya, A.; Plata, R. E.; Villarreal, V.; Muramulla, S.; Wu, J. Tetrahedron Lett. 2006, 47, 505. doi: 10.1016/j.tetlet.2005.11.063
37. [37]
  Reay, A. J.; Fairlamb, I. J. S. Chem. Commun. 2015, 51, 16289. doi: 10.1039/C5CC06980G
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