Chinese Journal of Organic Chemistry >
Aminolysis of Esters Using Quaternary Ammonium Salts as Amine Sources via Twice C-N Bond Activations
Received date: 2016-12-06
Revised date: 2017-02-13
Online published: 2017-03-03
Supported by
Project supported by the National Natural Science Foundation of China (No. 21462031), the Initial Special Research for National Basic Research Program of China (No. 2014CB460609) and the Research Program of Science and Technology at University of Inner Mongolia Autonomous Region (No. NJZZ14032).
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.
Key words： quaternary ammonium salts; aminolysis; palladium; C-N activation; aryl esters
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
[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] Bai, C. H.; Yao, X. F.; Li, Y. W. ACS Catal. 2015, 5, 884.
[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] Arefi, M.; Saberi, D.; Karimi, M.; Heydari, A. ACS Comb. Sci. 2015, 17, 341.
[5] Ouyang, K.; Hao, W.; Zhang, W. X.; Xi, Z. Chem. Rev. 2015, 115, 12045.
[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] (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] Xu, K.; Hu, Y. B.; Zhang, S.; Zha, Z. G.; Wang, Z. Y. Chem.-Eur. J. 2012, 18, 9793.
[9] Du, B.; Sun, P. Sci. China Chem. 2014, 57, 1176.
[10] Gao, L.; Tang, H.; Wang, Z. Chem. Commun. 2014, 50, 4085.
[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] (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] (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] (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] (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] Blakey, S. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 6046.
[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] Zhang, X. Q.; Wang, Z.-X. Org. Biomol. Chem. 2014, 12, 1448.
[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] 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.
[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.
[22] Sun, J. W.; Fu, Y. S.; He, G. Y.; Sun, X. Q.; Wang, X. Catal. Sci. Technol. 2014, 4, 1742.
[23] Pillo, T.; Zimmermann, R.; Steiner, P.; Hüfner, S. J. Phys.: Condens. Matter 1997, 9, 3987.
[24] Murata, S.; Miura, M.; Nomura, M. J. Org. Chem. 1989, 54, 4700.
[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] Guo, S. M.; Qian, B.; Xie, Y. J.; Xia, C. G.; Huang, H. M. Org. Lett. 2011, 13, 522.
[27] Zhang, D. L.; Bao, Z.; Bao, Y. S. J. Phys. Chem. C 2015, 119, 20426.
[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] Houghton, R. P.; Williams, C. S. Tetrahedron Lett. 1967, 40, 3929.
[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.
[31] Chow, C. T.; Chi, J. Y. Acta Chim. Sinica 1962, 28, 236 (in Chinese). (周啓霆, 嵇汝运, 化学学报, 1962, 28, 236.)
[32] Wu, K.; Huang, Z. L.; Ma, Y. Y.; Lei, A. W. RSC Adv. 2016, 6, 24349.
[33] Pathak, U.; Bhattacharyya, S.; Pandey, L. K.; Mathur, S.; Jain, R. RSC Adv. 2014, 4, 3900.
[34] Fang, T.; Gao, X. H.; Tang, R. Y.; Zhang, X. G.; Deng, C. L. Chem. Commun. 2014, 50, 14775.
[35] Bao, Y. S.; Bao, A.; Bao, Z.; Bai, Y.; Jia, M. J. Org. Chem. 2014, 79, 803.
[36] Bhattacharya, A.; Plata, R. E.; Villarreal, V.; Muramulla, S.; Wu, J. Tetrahedron Lett. 2006, 47, 505.
[37] Reay, A. J.; Fairlamb, I. J. S. Chem. Commun. 2015, 51, 16289.
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