Citation: Hai-Liang Hou, Fang-Li Qiu, An-Guo Ying, Song-Lin Xu. DABCO-based ionic liquids: Green and efficient catalysts with a dual catalytic role for aza-Michael addition[J]. Chinese Chemical Letters, ;2015, 26(3): 377-381. doi: 10.1016/j.cclet.2014.11.018 shu

DABCO-based ionic liquids: Green and efficient catalysts with a dual catalytic role for aza-Michael addition

1.
a School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China;
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b School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China

Corresponding author: An-Guo Ying, Song-Lin Xu,
Received Date: 28 September 2014
Available Online: 28 October 2014
Fund Project: and Zhejiang Provincial Natural Science Foundation of China (No. LY12B02004). (No. 2012E10033)

Four recoverable and reusable ionic liquids based on 1,4-diazobicyclo[2.2.2]octane (DABCO) have been synthesized to catalyze the aza-Michael addition of secondary amines to α,β-unsaturated compounds. Among the catalysts tested, [DABCO-PDO][OAc] was found to be most suitable for the reaction of a wide range of cyclic substrates without any solvent at room temperature, and afford the products in good to excellent yields within an appropriate amount of time. The proposed mechanism for the dual activation of the catalyst was supported by experimental results as well as the DFT calculation. In addition, the ionic liquids used can be regenerated and recycled several times without any loss of activity.
- Ionic liquid,
- Aza-Michael addition,
- Dual activitation,
- Recyclability
1. [1]
  [1] L.W. Xu, C.G. Xia, X.X. Hu, An efficient and inexpensive catalyst system for the aza-Michael reactions of enones with carbamates, Chem. Commun. 20 (2003) 2570-2571.
2. [2]
  [2] V. Kapras, R. Pohl, I. Císařová, U. Jahn, Asymmetric domino aza-Michael addition/[3+2] cycloaddition reactions as a versatile approach to α, β, γ-triamino acid derivatives, Org. Lett. 16 (2014) 1088-1091.
3. [3]
  [3] M.L. Kantama, M. Roy, S. Roy, B. Sreedhar, R.L. De, Polyaniline supported CuI: an efficient catalyst for C-N bond formation by N-arylation of N(H)-heterocycles and benzyl amines with aryl halides and arylboronic acids, and aza-Michael reactions of amines with activated alkenes, Catal. Commun. 9 (2008) 2226-2230.
4. [4]
  [4] D. Bandyopadhyay, S. Mukherjee, L.C. Turrubiartes, B.K. Banik, Ultrasoundassisted aza-Michael reaction in water: a green procedure, Ultrason. Sonochem. 19 (2012) 969-973.
5. [5]
  [5] N. Morimoto, Y. Takeuchi, Y. Nishina, Ionic amino acids: application as organocatalysts in the aza-Michael reaction, J. Mol. Catal. A: Chem. 368 (2013) 31-37.
6. [6]
  [6] T.K.T. Truong, G. Vo-Thanh, Synthesis of functionalized chiral ammonium, imidazolium, and pyridinium-based ionic liquids derived from (-)-ephedrine using solvent-free microwave activation. Applications for the asymmetric Michael addition, Tetrahedron 66 (2010) 5277-5282.
7. [7]
  [7] Y.Dai, B.D.Li,H.D.Quan, C.X.Lü, [Hmim]₃PW₁₂O₄0: ahigh-efficientandgreencatalyst for the acetalization of carbonyl compounds, Chin. Chem. Lett. 21 (2010) 678-681.
8. [8]
  [8] D.E. Siyutkin, A.S. Kucherenko, S.G. Zlotin, A new (S)-prolinamide modified by an ionic liquid moiety—a high performance recoverable catalyst for asymmetric aldol reactions in aqueous media, Tetrahedron 66 (2010) 513-518.
9. [9]
  [9] A.G. Ying, L. Liu, G.F. Wu, et al., Aza-Michael addition of aliphatic or aromatic amines to a, b-unsaturated compounds catalyzed by a DBU-derived ionic liquid under solvent-free conditions, Tetrahedron Lett. 50 (2009) 1653-1657.
10. [10]
  [10] S. Sahler, H. Konnerth, N. Knoblauch, M.H.G. Prechtl, Hydrogen storage in amine boranes: ionic liquid supported thermal dehydrogenation of ethylene diamine bisborane, Int. J. Hydrogen Energy 38 (2013) 3283-3290.
11. [11]
  [11] X. Zheng, Y.B. Qian, Y.M. Wang, 2-Pyrrolidinecarboxylic acid ionic liquid as a highly efficient organocatalyst for the asymmetric one-pot Mannich reaction, Eur. J. Org. Chem. 2010 (2010) 515-522.
12. [12]
  [12] E.V. Matveeva, P.V. Petrovskii, Z.S. Klemenkova, N.A. Bondarenko, I.L. Odinets, A practical and efficient green synthesis of β-aminophosphoryl compounds via the aza-Michael reaction in water, Comptes Rendus Chimie 13 (2010) 964-970.
13. [13]
  [13] A.G. Ying, Y.X. Ni, S.L. Xu, et al., Novel DABCO based ionic liquids: green and efficient catalysts with dual catalytic roles for aqueous Knoevenagel condensation, Ind. Eng. Chem. Res. 53 (2014) 5678–5682.
14. [14]
  [14] A.G. Ying, Z.F. Li, J.G. Yang, et al., DABCO based ionic liquids: recyclable catalysts for aza-Michael addition of alpha, beta-unsaturated amides under solvent-free conditions, J. Org. Chem. 79 (2014) 6510–6516.
15. [15]
  [15] K.P. Dhake, P.J. Tambade, R.S. Singhal, B.M. Bhanage, Promiscuous Candida Antarctica lipase B-catalyzed synthesis of β-amino esters via aza-Michael addition of amines to acrylates, Tetrahedron Lett. 51 (2010) 4455–4458.
16. [16]
  [16] S. Hussain, S.K. Bharadwaj, M.K. Chaudhuri, H. Kalita, Borax as an efficient metalfree catalyst for hetero-Michael reactions in an aqueous medium, Eur. J. Org. Chem. 2007 (2007) 374–378.
17. [17]
  [17] V.R. Choudhary, D.K. Dumbre, S.K. Patil, FeCl₃/Montmorillonite K10 as an efficient catalyst for solvent-free aza-Michael reaction between amine and a, b-unsaturated compounds, RSC Adv. 2 (2012) 7061–7065.
18. [18]
  [18] X. Liu, M. Lu, G. Gu, T. Lu, Aza-Michael reactions in water using functionalizedionic liquids as the recyclable catalysts, J. Iran. Chem. Soc. 8 (2011) 775–781.
19. [19]
  [19] M. Dabiri, P. Salehi, M. Bahramnejad, M. Baghbanzadeh, Ecofriendly and efficient procedure for hetero-Michael addition reactions with an acidic ionic liquid as catalyst and reaction medium, Monatsh Chem. 143 (2012) 109–112.
20. [20]
  [20] S. Mori, M. Ue, K. Ida, Electrolyte for aluminum electrolytic capacitor, US Patent US4774011 (1988).
21. [21]
  [21] H. Guo, J.L. Wang, X. Li, D.S. Lü, X.F. Lin, Oxa-Michael addition catalyzed by amidebased acidic ionic liquids, Chin. J. Catal. 32 (2011) 162–165.
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