Citation: Mohammad Javaherian, Foad Kazemi, Masoumeh Ghaemi. A dicationic, podand-like, ionic liquid water system accelerated copper-catalyzed azide-alkyne click reaction[J]. Chinese Chemical Letters, ;2014, 25(12): 1643-1647. doi: 10.1016/j.cclet.2014.09.005 shu

A dicationic, podand-like, ionic liquid water system accelerated copper-catalyzed azide-alkyne click reaction

a.
a. Department of Chemistry, College of Science, Shahid Chamran University, Ahvaz, Iran;
b.
b. Department of Chemistry, University for Advanced Studies in Basic Sciences, Iran

Corresponding author: Mohammad Javaherian,
Received Date: 8 April 2014
Available Online: 30 July 2014
Fund Project: Authors thank the Shahid Chamran University of Ahvaz for its financial support (No. 2013). (No. 2013)

In this work, an effective, task specific, dicationic, podand-like ionic liquid was synthesized and applied to improve the capability features of click reaction. Moreover, to broaden the scope and decreasing the serious limitations of preparation methods of organic azides, a simple green procedure for the preparation of alkyl azides, the fundamental starting materials in click reactions, from alcohols under solvent-free conditions and microwave irradiation has been reported, for the first time.
- Dicationic ionic liquid,
- Click chemistry,
- 1,2,3-Triazoles,
- Alkyl azides,
- Alkynes,
- Microwave irradiation
References
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  [26] I. Jlalia, C. Beauvineau, S. Beauvié re, et al., Automated synthesis of a 96 productsized library of triazole derivatives using a solid phase supported copper catalyst, Molecules 15 (2010) 3087-3120.
1. [1]
  [1] K. Banert, J. Wutke, T. Rü ffer, H. Lang, The alkyne azide click chemistry as a synthetic tool for the generation of cage-like triazole compounds, Synthesis 16 (2008) 2603-2609.
2. [2]
  [2] H.C. Kolb, M.G. Finn, K.B. Sharpless, Click chemistry: diverse chemical function from a few good reactions, Angew. Chem. Int. Ed. 40 (2001) 2004.
3. [3]
  [3] V.V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, Efficiency and fidelity in a click-chemistry route to triazole dendrimers by the copper(I)-catalyzed ligation of azides and alkynes, Angew. Chem. Int. Ed. 41 (2002) 2596-2599.
4. [4]
  [4] Y. Pu, H. Yuan, M. Yang, B. He, Z. Gu, Synthesis of peptide determine with polyhedral oligomeric silsesquioxane cores via click chemistry, Chin. Chem. Lett. 24 (2013) 917-920.
5. [5]
  [5] G. Tron, T. Pirali, R. Billington, et al., Click chemistry reactions in medicinal chemistry: applications of the 1,3-dipolar cycloaddition between azides and alkynes, Med. Res. Rev 28 (2008) 278-308.
6. [6]
  [6] H. Guo, F. Yang, Z. Jiao, J. Lin, Click synthesis and dye extraction properties of novel thiacalix[4]arene derivatives with triazolyl and hydrogen bonding groups, Chin. Chem. Lett. 24 (2013) 450-452.
7. [7]
  [7] M. Meldal, C.W. TornØe, Cu-catalyzed azide-alkyne cycloaddition, Chem. Rev. 108 (2008) 2952-3015.
8. [8]
  [8] A. Marra, A. Vecchi, C. Chiappe, B. Melai, A. Dondoni, Validation of the copper(I)-catalyzed azide-alkyne coupling in ionic liquids. Synthesis of a triazole-linked disaccharide as a case study, J. Org. Chem. 73 (2008) 2458-2461.
9. [9]
  [9] A.H. Jadhav, H. kim, A mild, efficient, and selective deprotection of tert-butyldimethylsilyl (TBDMS) ethers using dicationic ionic liquid as a catalyst, Tetrahedron Lett. 53 (2012) 5338-5342.
10. [10]
  [10] M. Messali, Z. Moussa, A.Y. Alzahrani, et al., Synthesis, characterization and the antimicrobial activity of new eco-friendly ionic liquids, Chemosphere 91 (2013) 1627-1634.
11. [11]
  [11] B.C. Ranu, S. Banerjee, Ionic liquid as catalyst and reaction medium. The dramatic influence of a task-specific ionic liquid, [bmIm]OH, in michael addition of active methylene compounds to conjugated ketones, carboxylic esters, and nitriles, Org. Lett. 7 (2005) 3049-3052.
12. [12]
  [12] A. Chinnappan, H. Kim, Environmentally benign catalyst: synthesis, characterization, and properties of pyridinium dicationic molten salts (ionic liquids) and use of application in esterification, Chem. Eng. J. 187 (2012) 283-288.
13. [13]
  [13] F. Kazemi, A.R. Massah, M. Javaherian, Chemoselective and scalable preparation of alkyl tosylates under solvent-free conditions, Tetrahedron 63 (2007) 5083-5087.
14. [14]
  [14] Q. Lin, W. Jiang, H. Fu, et al., Hydroformylation of higher olefin in halogen-free ionic liquids catalyzed by water-soluble rhodium-phosphine complexes, Appl. Catal. A: Gen. 328 (2007) 83-87.
15. [15]
  [15] H.C. Kolb, K.B. Sharpless, The growing impact of click chemistry on drug discovery, DDT 8 (24) (2003) 1128-1137.
16. [16]
  [16] J.R. Johansson, P. Lincoln, B. Nordé n, N. Kann, Sequential one-pot rutheniumcatalyzed azide-alkyne cycloaddition from primary alkyl halides and sodium azide, J. Org. Chem. 76 (2011) 2355-2359.
17. [17]
  [17] N. Miyaura, K. Yamada, A. Suzuki, A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides, Tetrahedron Lett. 36 (1979) 3437-3440.
18. [18]
  [18] D. Milstein, J.K. Stille, A general, selective, and facile method for ketone synthesis from acid chlorides and organotin compounds catalyzed by palladium, J. Am. Chem. Soc. 100 (1978) 3636-3638.
19. [19]
  [19] P.L. Golas, K. Matyjaszewski, Marrying click chemistry with polymerization: expanding the scope of polymeric materials, Chem. Soc. Rev. 39 (2010) 1338-1354.
20. [20]
  [20] S. Chassaing, M. Kumarraja, A.S.S. Sido, P. Pale, Click chemistry in CuI-zeolites: the huisgen [3+2] cycloaddition, J. Org. Lett. 9 (5) (2007) 883-886.
21. [21]
  [21] S. Chandrasekhar, M. Seenaiah, A. Kumar, et al., Intramolecular copper(I)-catalyzed 1, 3-dipolar cycloaddition of azido-alkynes: synthesis of triazolo-benzoxazepine derivatives and their biological evaluation, Tetrahedron Lett. 52 (2011) 806-808.
22. [22]
  [22] H. Ankati, E. Biehl, Microwave-assisted benzyne-click chemistry: preparation of 1H-benzo[d][1, 2,3]triazoles, Tetrahedron Lett. 50 (2009) 4677-4682.
23. [23]
  [23] J.E. Hein, L.B. krasnova, M. Iwasaki, V.V. Fokin, Cu-catalyzed azide-alkyne cycloaddition: preparation of tris((1-benzyl-1H-1,2,3-triazolyl)methyl) amine, Org. Synth. 88 (2012) 238-241.
24. [24]
  [24] H. Sharghi, R. Khalifeh, M.M. Doroodmand, Copper nanoparticles on charcoal for multicomponent catalytic synthesis of 1,2,3-triazole derivatives from benzyl halides or alkyl halides, terminal alkynes and sodium azide in water as a “green” solvent, Adv. Synth. Catal. 351 (2009) 207-218.
25. [25]
  [25] J. Raushel, V.V. Fokin, Efficient synthesis of 1-sulfonyl-1,2,3-triazoles, Org. Lett. 12 (21) (2010) 4952-4955.
26. [26]
  [26] I. Jlalia, C. Beauvineau, S. Beauvié re, et al., Automated synthesis of a 96 productsized library of triazole derivatives using a solid phase supported copper catalyst, Molecules 15 (2010) 3087-3120.
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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

A dicationic, podand-like, ionic liquid water system accelerated copper-catalyzed azide-alkyne click reaction

References

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通讯作者: 陈斌, bchen63@163.com