Solvent-Free Selective Cross-Aldol Condensation of Ketones with Aromatic Aldehydes Efficiently Catalyzed by a Reusable Supported Acidic Ionic Liquid

doi:10.1016/S1872-2067(11)60470-1

Abstract

Abstract: A newly prepared catalyst consisting of acidic ionic liquid 1-(4-sulfonic acid)butylpyridinium hydrogen sulfate supported on silica was used to catalyze the cross-aldol condensation of ketones with aromatic aldehydes under solvent-free conditions. The highly active and selective catalyst gave good to excellent yields of the desired cross-aldol products without the occurrence of any self-condensation reactions. Reaction times were short, the procedure and work-up were simple, and no volatile or hazardous organic solvents were necessary. Moreover, the catalyst could be reused at least four times with only a slight reduction in activity.

Key words: cross-aldol condensation, solvent-free condition, supported acidic ionic liquid, ketone, aromatic aldehyde

Abolghasem DAVOODNIA, Ghazaleh YASSAGHI. Solvent-Free Selective Cross-Aldol Condensation of Ketones with Aromatic Aldehydes Efficiently Catalyzed by a Reusable Supported Acidic Ionic Liquid[J]. Chinese Journal of Catalysis, 2012, 33(12): 1950-1957.

×
share this article

Add to citation manager EndNote|Ris|BibTeX

URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(11)60470-1

https://www.cjcatal.com/EN/Y2012/V33/I12/1950

References

1 Deli J, Lorand T, Szabo D, Foldesi A. Pharmazie, 1984, 39: 539
2 Leonard N J, Miller L A, Berry J W. J Am Chem Soc, 1957, 79: 1482
3 Dimmock J R, Padmanilayam M P, Zello G A, Neinaber K H, Allen T M, Santos C L, De Clercq E, Balzarini J, Manavathu E K, Stables J P. Eur J Med Chem, 2003, 38: 169
4 Gangadhara, Kishore K. Polymer, 1995, 36: 1903
5 Robinson T P, Ehlers T, Hubbard R B, Bai X, Arbiser J L, Goldsmith D J, Bowena J P. Bioorg Med Chem Lett, 2003, 13: 115
6 Dinkova-Kostova A T, Abeygunawardana C, Talalay P. J Med Chem, 1998, 41: 5287
7 Piantadosi C, Hall I H, Irvine J L, Carlson G L. J Med Chem, 1973, 16: 770
8 Raj A A, Raghunathan R, Sridevi Kumari M R, Raman N. Bioorg Med Chem, 2003, 11: 407
9 Girgis A S, Ibrahim Y A, Mishriky N, Lisgarten J N, Potter B S, Palmer R A. Tetrahedron, 2001, 57: 2015
10 Rovnyak G, Shu V, Schwartz J. J Heterocycl Chem, 1981, 18: 327
11 Amarasekara A S. Tetrahedron Lett, 2005, 46: 2635
12 Drexler M T, Amiridis M D. J Catal, 2003, 214: 136
13 Karthikeyan M S, Holla B S, Kumari N S. Eur J Med Chem, 2007, 42: 30
14 Rateb N M. Phosphorus, Sulfur Silicon Relat Elem, 2007, 182: 2393
15 Ducki S, Forrest R, Hadfield J A, Kendall A, Lawrence N J, McGown A T, Rennison D. Bioorg Med Chem Lett, 1998, 8: 1051
16 Mishra N, Arora P, Kumar B, Mishra L C, Bhattacharya A, Awasthi S K, Bhasin V K. Eur J Med Chem, 2008, 43: 1530
17 Wattenberg L W, Coccia J B, Galbraith A R. Cancer Lett, 1994, 83: 165
18 Dimmock J R, Elias D W, Beazel M A, Kandepu N M. Curr Med Chem, 1999, 6: 1125
19 Sipos G, Sirokman F. Nature, 1964, 202: 489
20 Kozlov N G, Basalaeva L I. Russ J Gen Chem, 2004, 74: 926
21 Le Gall E, Texier-Boullet F, Hamelin J. Synth Commun, 1999, 29: 3651
22 Li J T, Chen G F, Wang J X, Li T S. Synth Commun, 1999, 29: 965
23 Sivakumar P M, Seenivasan S P, Kumar V, Doble M. Bioorg Med Chem Lett, 2007, 17: 1695
24 Wan Y, Chen X M, Pang L L, Ma R, Yue C H, Yuan R, Lin W, Yin W, Bo R C, Wu H. Synth Commun, 2010, 40: 2320
25 Yang S D, Wu L Y, Yan Z Y, Pan Z L, Liang Y M. J Mol Catal A, 2007, 268: 107
26 Jana S K. Catal Surv Asia, 2005, 9: 25
27 Davoodnia A, Heravi M M, Rezaei-Daghigh L, Tava-koli-Hoseini N. Chin J Chem, 2010, 28: 429
28 Narender T, Papi Reddy K. Tetrahedron Lett, 2007, 48: 3177
29 Salehi P, Khodaei M M, Zolfigol M A, Keyvan A. Monatsh Chem, 2002, 133: 1291
30 Rostami A, Ahmad-Jangi F. Chin Chem Lett, 2011, 22: 1029
31 Wang L, Sheng J, Tian H, Han J, Fan Z, Qian C. Synthesis, 2004, 18: 3060
32 Deng G, Ren T. Synth Commun, 2003, 33: 2995
33 Sharma S K, Parikh P A, Jasra R V. J Mol Catal A, 2007, 278: 135
34 Zhu Y W, Yi W B, Cai C. J Fluorine Chem, 2011, 132: 71
35 Zheng M, Wang L, Shao J, Zhong Q. Synth Commun, 1997, 27: 351
36 Nakano T, Irifune S, Umano S, Inada A, Ishii Y, Ogawa M. J Org Chem, 1987, 52: 2239
37 Motiur Rahman A F M, Jeong B S, Kim D H, Park J K, Lee E S, Jahng Y. Tetrahedron, 2007, 63: 2426
38 Hazarkhani H, Kumar P, Kondiram K S, Shafi Gadwal I M. Synth Commun, 2010, 40: 2887
39 Lin P, Li B, Li J, Wang H, Bian X, Wang X. Catal Lett, 2011, 141: 459
40 Rawal K, Mishra M K, Dixit M, Srinivasarao M. J Ind Eng Chem, 2012, 18: 1474
41 An L T, Zou J P, Zhang L L. Catal Commun, 2008, 9: 349
42 Shrikhande J J, Gawande M B, Jayaram R V. Catal Commun, 2008, 9: 1010
43 Yadav J S, Reddy B V S, Nagaraju A, Sarma J A R P. Synth Commun, 2002, 32: 893
44 Moghaddas M, Davoodnia A, Heravi M M, Tavakoli-Hoseini N. Chin J Catal, 2012, 33: 706
45 Tavakoli-Hoseini N, Davoodnia A. Asian J Chem, 2010, 22: 7197
46 Heravi M M, Saeedi M, Karimi N, Zakeri M, Beheshtiha Y S, Davoodnia A. Synth Commun, 2010, 40: 523
47 Seifi N, Zahedi-Niaki M H, Reza Barzegari M, Davoodnia A, Zhiani R, Kaju A A. J Mol Catal A, 2006, 260: 77
48 Davoodnia A. Asian J Chem, 2010, 22: 1595
49 Norouzi H, Davoodnia A, Bakavoli M, Zeinali-Dastmalbaf M, Tavakoli-Hoseini N, Ebrahimi M. Bull Korean Chem Soc, 2011, 32: 2311
50 Zeinali-Dastmalbaf M, Davoodnia A, Heravi M M, Tava-koli-Hoseini N, Khojastehnezhad A, Zamani H A. Bull Korean Chem Soc, 2011, 32: 656
51 Tavakoli-Hoseini N, Davoodnia A. Chin J Chem, 2011, 29: 203
52 Khojastehnezhad A, Davoodnia A, Bakavoli M, Tava-koli-Hoseini N, Zeinali-Dastmalbaf M. Chin J Chem, 2011, 29: 297
53 Mohammadzadeh-Dehsorkh N, Davoodnia A, Tava-koli-Hoseini N, Moghaddas M. Synth React Inorg Met-Org Nano-Met Chem, 2011, 41: 1135
54 Davoodnia A, Tavakoli-Nishaburi A, Tavakoli-Hoseini N. Bull Korean Chem Soc, 2011, 32: 635
55 Yassaghi G, Davoodnia A, Allameh S, Zare-Bidaki A, Tavakoli-Hoseini N. Bull Korean Chem Soc, 2012, 33: 2724

[1]	Abhishek R. Varma, Bhushan S. Shrirame, Sunil K. Maity, Deepti Agrawal, Naglis Malys, Leonardo Rios-Solis, Gopalakrishnan Kumar, Vinod Kumar. Recent advances in fermentative production of C4 diols and their chemo-catalytic upgrading to high-value chemicals [J]. Chinese Journal of Catalysis, 2023, 52(9): 99-126.
[2]	Zhi-Hua Zhou, Xiao Zhang, Yong-Fu Huang, Kai-Hong Chen, Liang-Nian He. Synthesis of α-hydroxy ketones by copper(I)-catalyzed hydration of propargylic alcohols: CO₂ as a cocatalyst under atmospheric pressure [J]. Chinese Journal of Catalysis, 2019, 40(9): 1345-1351.
[3]	Ahmed H. Aboo, Robina Begum, Liangliang Zhao, Zahoor H. Farooqi, Jianliang Xiao. Methanol as hydrogen source: Chemoselective transfer hydrogena-tion of α,β-unsaturated ketones with a rhodacycle [J]. Chinese Journal of Catalysis, 2019, 40(11): 1795-1799.
[4]	Rui Ma, Yunpeng Li, Guandong Wu, Yufei He, Junting Feng, Yingying Zhao, Dianqing Li. Fabrication of Pd-based metal-acid-alkali multifunctional catalysts for one-pot synthesis of MIBK [J]. Chinese Journal of Catalysis, 2018, 39(8): 1384-1394.
[5]	Liandi Wang, Tingting Liu. Ruthenium(Ⅱ) complex catalysts bearing a 2,6-bis(tetrazolyl)pyridine ligand for the transfer hydrogenation of ketones [J]. Chinese Journal of Catalysis, 2018, 39(2): 327-333.
[6]	Lu Wang, Wei Sun, Chao Liu. Cu-catalyzed deoxygenative gem-hydroborylation of aromatic aldehydes and ketones to access benzylboronic esters [J]. Chinese Journal of Catalysis, 2018, 39(11): 1725-1729.
[7]	Qing-Hua Li, Yuan Dong, Fei-Fei Chen, Lei Liu, Chun-Xiu Li, Jian-He Xu, Gao-Wei Zheng. Reductive amination of ketones with ammonium catalyzed by a newly identified Brevibacterium epidermidis strain for the synthesis of (S)-chiral amines [J]. Chinese Journal of Catalysis, 2018, 39(10): 1625-1632.
[8]	Jiaqiong Sun, Guangfan Zheng, Yongmei Fu, Qiao Zhang, Yimin Wang, Qian Zhang, Yan Li, Qian Zhang. Copper-catalyzed tandem radical amination/1, 2-carbon migration of allylic alcohols: Direct access to α-quaternary-β-amino ketones [J]. Chinese Journal of Catalysis, 2018, 39(1): 138-145.
[9]	Lanhui Ren, Lianyue Wang, Ying Lü, Guosong Li, Shuang Gao. Direct oxidation of the C_sp₃-H bonds of N-heterocyclic compounds to give the corresponding ketones using a reusable heterogeneous MnO_x-N@C catalyst [J]. Chinese Journal of Catalysis, 2016, 37(8): 1216-1221.
[10]	Tenglong Guo, Quanbin Jiang, Likun Yu, Zhengkun Yu. Synthesis of chalcones via domino dehydrochlorination/Pd(OAc)₂-catalyzed Heck reaction [J]. Chinese Journal of Catalysis, 2015, 36(1): 78-85.
[11]	Heshmatollah Alinezhad, Sahar Mohseni Tavakkoli, Pourya Biparva. Cu-doped ZnO nanocrystalline powder catalyzed one-pot synthesis of fully substituted new indeno[1,2-b]pyridines at room temperature by a multi-component reaction [J]. Chinese Journal of Catalysis, 2014, 35(4): 560-564.
[12]	DU Wangming, WANG Qingfu, YU Zhengkun. Ru(II) pyridyl-based NNN complex catalysts for (asymmetric) transfer hydrogenation of ketones at room temperature [J]. Chinese Journal of Catalysis, 2013, 34(7): 1373-1377.
[13]	DING Jiang-Hong, XU Le, XU Hao, WU Hai-Hong, LIU Yue-Ming, WU Peng. Highly Efficient Synthesis of Methyl Ethyl Ketone Oxime through Ammoximation over Ti-MOR Catalyst [J]. Chinese Journal of Catalysis, 2013, 34(1): 243-250.
[14]	MA Heng-Chang, WANG Feng, CAO Wei, BAO Zhi-Kang, MA Yuan, YANG Zhi-Wang, LEI Zi-Qiang. Preparation and Characterization of Wool-Pd(0) Catalyst and Its Catalytic Performance for Oxidation of Alcohol in Water [J]. Chinese Journal of Catalysis, 2012, 33(9): 1594-1600.
[15]	LUO Jian-Qing, TAN Rong, KONG Yu, LI Cheng-Yong, YIN Dong-Hong. Effect of Additives on L-Proline Catalyzed Direct Asymmetric Aldol Reactions [J]. Chinese Journal of Catalysis, 2012, 33(7): 1133-1138.