Novel basic ionic liquid based on alkylammonium as efficient catalyst for Knoevenagel reaction

Synthetic Communications

Volumn 42, Issue 9, 2012, Pages 1384-1391

  Zhou, Shuai ^a   Liu, Lu ^a   Wang, Bo ^a   Ma, Mingguo ^a   Xu, Feng ^a   Sun, Runcang ^a,b  

^a BEIJING FORESTRY UNIVERSITY   (China)

^b SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Basic ionic liquid; Dual function; Knoevenagel condensation; Tetramethylethylenediamine

Indexed keywords

ACETIC ACID DERIVATIVE; AMMONIA; BENZALDEHYDE; IONIC LIQUID; N,N,N',N' TETRAMETHYL N' HEXYLETHYLENEDIAMMONIUM TETRAFLUOROBORIC ACID; NUCLEOPHILE; SOLVENT; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; GREEN CHEMISTRY; KNOEVENAGEL CONDENSATION; TEMPERATURE;

EID: 84863120119     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.540692     Document Type: Article

References (25)

1. Pârvulescu, V. I.; Hardacre, C. Catalysis in ionic liquids. Chem. Rev. 2007, 107, 2615-2665. (Pubitemid 47029102)
2. Akaiyama, T.; Suzuki, A.; Fuchibe, K. Mannich-type reaction promoted by an ionic liquid. Synlett. 2005, 6, 1024-1026. (Pubitemid 40524281)
3. Yadav, L. D. S.; Awasthi, C.; Rai, A. Ionic liquid-promoted one-pot oxidative Michael addition of TMSCN to Baylis-Hillman adducts. Tetrahedron Lett. 2008, 49, 6360-6363.
4. Ranu, B. C.; Banerjee, S.; Jana, R. Ionic liquid as catalyst and solvent: The remarkable effect of a basic ionic liquid, [bmIm]OH on Michael addition and alkylation of active methylene compounds. Tetrahedron 2007, 63(3), 776-782. (Pubitemid 44881046)
5. Wang, C.; Zhao, W.; Li, H.; Guo, L. Solvent-free synthesis of unsaturated ketones by the Saucy-Marbet reaction using simple ammonium ionic liquid as a catalyst. Green Chem. 2009, 11, 843-847.
6. Xiao, L. F.; Yue, Q. F.; Xia, C. G.; Xu, L. W. Supported basic ionic liquid: Highly effective catalyst for the synthesis of 1,2-propylene glycol from hydrolysis of propylene carbonate. J. Mol. Catal. A: Chem. 2008, 279(2), 230-234.
7. Zang, H. J.; Wang, M. L.; Cheng, B. W. Song, J. Ultrasound-promoted synthesis of oximes catalyzed by a basic ionic liquid [bmIm]OH. Ultrason. Sonochem. 2009, 16(3), 301-303.
8. Ranu, B. C.; Jana, R.; Sowmiah, S. An improved procedure for the three-component synthesis of highly substituted pyridines using ionic liquid. J. Org. Chem. 2007, 72(8), 3152-3154. (Pubitemid 46624462)
9. Xu, J. M.; Liu, B. K.; Wu, W. B.; Qian, C.; Wu, Q.; Lin, X. F. Basic ionic liquid as catalysis and reaction medium: A novel and green protocol for the markovnikov addition of n-heterocycles to vinyl esters, using a task-specific ionic liquid, [bmim]OH. J. Org. Chem. 2006, 71(10), 3991-3993.
10. Jones, G. In Organic Reactions; A. C. Cope (Ed.); John & Sons: New York, 1967, vol. 15, p. 204.
11. Lai, G. Q.; Peng, J. J.; Li, J. Y.; Qiu, H. Y.; Jiang, J. X.; Jiang, K. Z.; Shen, Y. J. Ionic liquid functionalized silica gel: Novel catalyst and fixed solvent. Tetrahedron Lett. 2006, 47(39), 6951-6953.
12. Wang, Y.; Shang, Z. C.; Wu, T. X.; Fan, J. C.; Chen, X. Synthetic and theoretical study on proline-catalyzed Knoevenagel condensation in ionic liquid. J. Mol. Catal. A: Chem. 2006, 253(1-2), 212-221. (Pubitemid 43783423)
13. Xin, X.; Guo, X.; Duan, H. F.; Lin, Y. J.; Sun, H. Efficient Knoevenagel condensation catalyzed by cyclic guanidinium lactate ionic liquid as medium. Catal. Commun. 2007, 8(2), 115-117. (Pubitemid 46038831)
14. Yue, C. B.; Mao, A. Q.; Wei, Y. Y.; Lü, M. J. Knoevenagel condensation reaction catalyzed by task-specific ionic liquid under solvent-free conditions. Catal, Commun. 2008, 9(7), 1571-1574.
15. 4] ionic liquid. Catal. Commun. 2008, 9(8), 1779-1781.
16. Chen, X. W.; Li, X. H.; Song, H. B.; Lü, Y. X.; Wang, F. R.; Hu, A. X. Synthesis of a basic imidazolide ionic liquid and its application in catalyzing knoevenagel condensation. Chin. J. Catal. 2008, 29(10), 957-959.
17. 3 nanocrystallites: An efficient magnetic and recyclable heterogeneous catalyst for aqueous Knoevenagel condensation. J. Mol. Catal. A: Chem. 2009, 306(1-2), 107-112.
18. 3 nanoparticles functionalized with basic ionic liquids for aqueous Knoevenagel condensation. Appl. Catal. A: Gen. 2009, 366(1), 141-147.
19. Paun, C.; Barklie, J.; Goodrich, P.; Gunaratne, H. Q. N.; McKeown, A.; Pârvulescu, V. I.; Hardacre, C. Supported and liquid phase task specific ionic liquids for base catalysed Knoevenagel reactions. J. Mol. Catal. A: Chem. 2007, 269(1-2), 64-71. (Pubitemid 46507866)
20. Zhao, H. H.; Yu, N. Y.; Ding, Y.; Tan, R.; Liu, C.; Yin, D. H.; Qiu, H. Y.; Yin, D. L. Task-specific basic ionic liquid immobilized on mesoporous silicas: Efficient and reusable catalysts for Knoevenagel condensation in aqueous media. Microporous Mesoporous Mater. 2010, 136(1-3), 10-17.
21. 4 ionic liquid: A novel reaction medium for the synthesis of β-amino alcohols. Tetrahedron Lett. 2003, 44(5), 1047-1050. (Pubitemid 36183234)
22. Parida, K. M.; Rath, D. Amine functionalized MCM-41: An active and reusable catalyst for Knoevenagel condensation reaction. J. Mol. Catal. A: Chem. 2009, 310(1-2), 93-100.
23. Fang, D.; Cheng, J.; Fei, Z. H.; Gong, K.; Liu, Z. L. Synthesis of chalcones via Claisen-Schmidt condensation reaction catalyzed by acyclic acidic ionic liquids. Catal. Commun. 2008, 9(9), 1924-1927.
24. Shen, J. H.; Wang, H. H.; Liu, H. C.; Sun, Y.; Liu, Z. M. Brønsted acidic ionic liquids as dual catalyst and solvent for environmentally friendly synthesis of chalcone. J. Mol. Catal. A: Chem. 2008, 280(1-2), 24-28.
25. Yang, S. D.; Wu, L. Y.; Yan, Z. Y.; Pan, Z. L.; Liang, Y. M. A novel ionic liquid-supported organocatalyst of pyrrolidine amide: Synthesis and catalyzed Claisen-Schmidt reaction. J. Mol. Catal. A: Chem. 2007, 268(1-2), 107-111.