Silver-catalyzed three-component reaction of phenyldiazoacetate with arylamine and imine

doi:10.1016/S1872-2067(18)63088-8

Chinese Journal of Catalysis ›› 2018, Vol. 39 ›› Issue (10): 1594-1598.DOI: 10.1016/S1872-2067(18)63088-8

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Silver-catalyzed three-component reaction of phenyldiazoacetate with arylamine and imine

Bai-Ling Chen^a,b, Zhen Wang^a, You-Can Zhang^a, Zhi-Gang Zhao^b, Zili Chen^a

a Department of Chemistry, Renmin University of China, Beijing 100872, China;
b College of Chemistry & Environment Protection Engineering, Southwest University for Nationalities, Chengdu 610041, Sichuan, China

Received:2018-03-26 Revised:2018-04-23 Online:2018-10-18 Published:2018-08-03
Contact: 10.1016/S1872-2067(18)63088-8
Supported by:
This work was supported by the National Natural Science Foundation of China (21472237).

Abstract

Abstract:

A new method was developed to diastereoselectively synthesize polysubstituted 1,2-diamine compounds from the reaction of diazoesters with arylamines and diaryl imines by using the dioxazoline ligand L₂-ligated silver catalyst. The Lewis acidity of the silver catalyst affected the different types of substrate diastereoselectivities; It also led to the formation of amine-exchange side products.

Key words: Silver catalysis, Carbene transfer reaction, Three-component reaction, Ammonium ylide, Diamine compouds

Bai-Ling Chen, Zhen Wang, You-Can Zhang, Zhi-Gang Zhao, Zili Chen. Silver-catalyzed three-component reaction of phenyldiazoacetate with arylamine and imine[J]. Chinese Journal of Catalysis, 2018, 39(10): 1594-1598.

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References

[1] M. P. Doyle, M. A. McKervey, T. Ye, Modem Catalytic Methods for Organic Synthesis with Diazo Compounds, John Wiley and Sons, New York, 1998, 652.
[2] A. Padwa, S. F. Hornbuckle, Chem. Rev., 1991, 91, 263-309.
[3] Y. H. Wang, Y. X. Zhu, Z. Y. Chen, A. Q. Mi, W. H. Hu, M. P. Doyle, Org. Lett., 2003, 5, 3923-3926.
[4] J. Jiang, X. Ma, C. Ji, Z. Guo, T. Shi, S. Liu, W. Hu, Chem. Eur. J., 2014, 20, 1505-1509.
[5] J. Jiang, H. D. Xu, J. B. Xi, B. Y. Ren, F. P. Lv, X. Guo, L. Q. Jiang, Z. Y. Zhang, W. H. Hu, J. Am. Chem. Soc., 2011, 133, 8428-8431.
[6] R. R. Lei, Y. Wu, S. Z. Dong, K. L. Jia, S. Y. Liu, W. H. Hu, J. Org. Chem. 2017, 82, 2862-2869.
[7] L. Q. Jiang, D. Zhang, Z. Q. Wang, W. H. Hu, Synthesis, 2013, 45, 452-458.
[8] T. D. Shi, X. Guo, S. H. Teng, W. H. Hu, Chem. Commun., 2015, 51, 15204-15207.
[9] L. Qiu, X. Guo, C. C. Jing, C. Q. Ma, S. Y. Liu, W. H. Hu, Chem. Commun., 2016, 52, 11831-11833.
[10] C. C. Jing, D. Xing, W. H. Hu, Chem. Commun., 2014, 50, 951-953.
[11] Y. H. Wang, Z. Y. Chen, A. Q. Mi, W. H. Hu, Chem. Commun., 2004, 2486-2487.
[12] J. B. Xi, M. L. Ma, W. H. Hu, Tetrahedron, 2016, 72, 579-583.
[13] Y. G. Zhu, C. W. Zhai, Y. L. Yue, L. P. Yang, W. H. Hu, Chem. Commun., 2009, 1362-1364.
[14] S. K. Jia, Y. B. Lei, L. L. Song, S. Y. Liu, W. H. Hu, Chin. Chem. Lett., 2017, 28, 213-217.
[15] H. X. Huang, Y. H. Wang, Z. Y. Chen, W. H. Hu, Adv. Synth. Catal., 2005, 347, 531-534.
[16] D. F. Chen, F. Zhao, Y. Hu, L. Z. Gong, Angew. Chem. Int. Ed., 2014, 53, 10763-10767.
[17] H. Qiu, M. Li, L. Q. Jiang, F. P. Lv, L. Zan, C. W. Zhai, M. P. Doyle, W. H. Hu, Nat. Chem., 2012, 4, 733-738.
[18] D. Zhang, J. Zhou, F. Xia, Z. H. Kang, W. H. Hu, Nat. Commun., 2014, 6, 5801-5808.
[19] S. K. Jia, D. Xing, D. Zhang, W. H. Hu, Angew. Chem. Int. Ed., 2014, 53, 13098-13101.
[20] Z. Wang, J. Wen, Q. W. Bi, X. Q. Xu, Z. Q. Shen, X. X. Li, Z. L. Chen, Tetrahedron Lett., 2014, 55, 2969-2972.
[21] Y. F. Liu, Z. Wang, J. W. Shi, B. L, Chen, Z. G. Zhao, Z. Chen, J. Org. Chem., 2015, 80, 12733-12739.
[22] K. Burgess, H. J. Lim, A. M. Porte, G. A. Sulikowski, Angew. Chem. Int. Ed., 1996, 35, 220-222.
[23] H. V. R. Dias, R. G. Browning, S. A. Polach, H. V. K. Diyabalanage, C. J. Lovely, J. Am. Chem. Soc., 2003, 125, 9270-9271.
[24] J. L. Thompson, H. M. L. Davies, J. Am. Chem. Soc., 2007, 129, 6090-6091.
[25] Y. J. Su, M. Lu, B. L. Dong, H. Chen, X. D. Shi, Adv. Synth. Catal., 2014, 356, 692-696.
[26] The relative stereochemistry of 4aa is same as the result of Rh(Ⅲ) catalyzed reaction. The minor product 4aa' has also been isolated (from the 5 mmol scale reaction) and characterized by using ¹H NMR & ¹³C NMR spectroscopy and HRMS.
[27] It was notable 4ba-4ha's diasteroselectivities are higher than the results of Rh(Ⅲ) catalyzed reaction reported in previous research.
[28] Compound 4ae' is inseparable from the N-H insertion product.
[29] Another type of possible amine-exchange side product, with phenylamine acting as the nucleophile, and N-(4-fluorophenyl)-1-(4-nitrophenyl)methanimine (the amine-exchange imine substrate) as the electrophile, was not observed in Eq (3)'s reaction. Eq (4)'s result is similar to Eq (3).

Silver-catalyzed three-component reaction of phenyldiazoacetate with arylamine and imine

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