Citation: Wang Fang, Feng Huangdi, Li Huiqiong, Miao Teng, Cao Tiantian, Zhang Min. 1D Fe₃O₄@CuSiO₃ composites catalyzed decarboxylative A³-coupling for propargylamine synthesis[J]. Chinese Chemical Letters, ;2020, 31(6): 1558-1563. doi: 10.1016/j.cclet.2019.11.004 shu

1D Fe₃O₄@CuSiO₃ composites catalyzed decarboxylative A³-coupling for propargylamine synthesis

College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620, China

hdfeng@sues.edu.cn

zhangmin@sues.edu.cn

Received Date: 17 September 2019
Revised Date: 3 November 2019
Accepted Date: 5 November 2019
Available Online: 6 November 2019

Figures(6)

Highly active and stable magnetic copper catalysts were successfully achieved by magnetic induced Stöber method and subsequent hydrothermal reaction with copper ions in alkaline condition. The high content of Cu²⁺ as well as the unique structures of hierarchical copper silicate in the as-prepared catalysts endowed their outstanding catalytic performance. Efficient decarboxylative A³-coupling of α-keto acid, amine and alkyne was realized with the low Fe₃O₄@CuSiO₃ loading. A range of propargylamines were produced in good to excellent yields under solvent-free condition. Moreover, the catalyst can be easily separated from the final organic product with an external magnet. Also, this kind of catalyst could be recycled up to six times while maintaining its activity.
- Magnetic copper catalyst,
- Heterogeneous catalysis,
- One-dimensional,
- Decarboxylative coupling,
- Propargylamines
1. [1]
  (a) J.J. Chen, D.M. Swope, J. Clin. Pharmacol. 45 (2005) 878-894;
  (b) M. Baranyi, P.F. Porceddu, F. Gölöncse'r, et al., Mol. Neurodegener.11 (2016) 1-21;
  (c) I. Bolea, A. Gella, M. Unzeta, J. Neural Transm. 120 (2013) 893-902;
  (d) F.T. Zindo, J. Joubert, S.F. Malan, Future Med. Chem. 7 (2015) 609-629;
  (e) K. Lauder, A. Toscani, N. Scalacci, D. Castagnolo, Chem. Rev. 117 (2017) 14091-14200;
  (f) V.A. Peshkov, O.P. Pereshivko, A.A. Nechaev, A.A. Peshkov, E.V. Vander Eycken, Chem. Soc. Rev. 47 (2018) 3861-3898.
2. [2]
  (a) X.X. Sun, C. Li, Y.Y. He, et al., Adv. Synth. Catal. 359 (2017) 2660-2670;
  (b) Y.M. Wang, H.H. Zhang, C. Li, T. Fan, F. Shi, Chem. Commun. 52 (2016) 1804-1807;
  (c) X.X.Sun, H.H.Zhang, G.H.Li, Y.Y.He, F.Shi, Chem.Eur.J.22 (2016)17526-17532.
3. [3]
  (a) C. Wei, Z. Li, C.J. Li, Synlett (2004) 1472-1483;
  (b) L. Zani, C. Bolm, Chem. Commun. 38 (2006) 4263-4275;
  (c) V.A. Peshkov, O.P. Pereshivko, E. Van der Eycken, Chem. Soc. Rev. 41 (2012) 3790-3807;
  (d) D. Seidel, Org. Chem. Front. 1 (2014) 426-429.
4. [4]
  (a) R. Shang, L. Liu, Sci. China Chem. 54 (2011) 1670-1687;
  (b) N. Rodríguez, L.J. Goossen, Chem. Soc. Rev. 40 (2011) 5030-5048;
  (c) J.D.Weaver, A.Recio, A.J.Grenning, J.A.Tunge, Chem.Rev.111(2011)1846-1913;
  (d) J. Schwarz, B. König, Green Chem. 20 (2018) 323-361;
  (e) H.D. Feng, H.H. Jia, Z.H. Sun, Adv. Synth. Catal. 357(2015) 2447-2452;
  (f) H.D. Feng, H.H. Jia, Z.H. Sun, J. Org. Chem. 79 (2014) 11812-17181.
5. [5]
  (a) F.L. Vaillant, T.J. Courant, Angew. Chem. Int. Ed. 54 (2015) 11200-11204;
  (b) H.Zhang, P.X. Zhang, M.Jiang, H.J.Yang, H.Fu, Org. Lett.19 (2017)1016-1019;
  (c)H.D.Feng, D.S.Ermolat'ev, G.H.Song, E.VanderEycken, J.Org.Chem.76 (2011) 7608-7613;
  (d) P.F. Zhao, H.D. Feng, H.R. Pan, Z.H. Sun, M.C. Tong, Org. Chem. Front. 4 (2017) 37-41.
6. [6]
  (a) H.P. Bi, L. Zhao, Y.M. Liang, C.J. Li, Angew. Chem. Int. Ed. 48 (2009) 792-795;
  (b) H.P. Bi, Q. Teng, M. Guan, et al., J. Org. Chem. 75 (2010) 783-788;
  (c) D. Chen, P. Huang, Y. Yu, et al., Chem. Commun. 47 (2011) 5801-5803;
  (d) H.D. Feng, D.S. Ermolat'ev, G.H. Song, E. Van der Eycken, J. Org. Chem. 77 (2012) 5149-5154;
  (e) H.D. Feng, D.S. Ermolat'ev, G.H. Song, E. Van der Eycken, Org. Lett.14 (2012) 1942-1945.
7. [7]
  (a) I. Luz, F.X.L. Xamena, A. Corma, J. Catal. 285 (2012) 285-291;
  (b) G. Bosica, R. Abdilla, J. Mol. Catal. A: Chem. 426 (2017) 542-549;
  (c) A.V. Nakhat, G.D. Yada, Mol. Catal. 451(2018) 209-219.
8. [8]
  (a) M.J. Aliaga, D.J. Ramón, M. Yus, Org. Biomol. Chem. 8 (2010) 43-46;
  (b) J.Y. Zhang, X. Huang, Q.Y. Shen, J.Y. Wang, G.H. Song, Chin. Chem. Lett. 29 (2018) 197-200.
9. [9]
  (a) U.C. Rajesh, U. Gulati, D.S. Rawat, ACS Sustainable Chem. Eng. 4 (2016) 3409-3419;
  (b) P. Kaur, B. Kumar, V. Kumar, R. Kumar, Tetrahedron Lett. 59 (2018) 1986-1991;
  (c) U. Gulati, U.C. Rajesh, N. Bunekar, D.S. Rawat, ACS Sustainable Chem. Eng. 5 (2017) 4672-4682;
  (d) U. Gulati, U.C. Rajesh, D.S. Rawat, ACS Sustainable Chem. Eng. 6 (2018) 10039-10051.
10. [10]
  (a) Y. Li, Y. Lu, C. Zhao, et al., Energy Storage Mater. 7 (2017) 130-151;
  (b) K.M. Kwok, S.W.D. Ong, L. Chen, H.C. Zeng, ACS Appl. Mater. Interface 9 (2017) 37210-37222.
11. [11]
  M. Srinivas, P. Srinivasu, S.K. Bhargava, M.L. Kantam, Catal. Today 208 (2013) 66-71. doi: 10.1016/j.cattod.2013.02.006
12. [12]
  (a) M. Zhang, Y.T. Wang, Y.W. Zhang, et al., Appl. Surf. Sci. 375 (2016) 154-161;
  (b) Y. Zhang, M. Zhang, J. Yang, L.J. Zheng, J.L. Xu, J. Alloys Compd. 695 (2017) 3256-3266;
  (c) M. Zhang, B.Y. Wang, W.Z. Li, W.J. Gan, Dalton Trans. 45 (2016) 922-927;
  (d) M. Zhang, T. Miao, J. Zheng, et al., Microporous Mesoporous Mater. 286 (2019) 207-213.
13. [13]
  J.W. Liu, J. Cheng, R.C. Che, et al., ACS Appl. Mater. Inter. 5 (2013) 2503-2509. doi: 10.1021/am3030432
14. [14]
  J. Choi, J. Lim, F.M. Irudayanathan, et al., Asian J. Org. Chem. 5 (2016) 770-777. doi: 10.1002/ajoc.201600109
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沈阳化工大学材料科学与工程学院沈阳 110142

1D Fe3O4@CuSiO3 composites catalyzed decarboxylative A3-coupling for propargylamine synthesis

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通讯作者: 陈斌, bchen63@163.com

1D Fe₃O₄@CuSiO₃ composites catalyzed decarboxylative A³-coupling for propargylamine synthesis