SCOPUS 정보 검색 플랫폼

Volumn 90, Issue 3, 2012, Pages 290-297

Ionic-liquid-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene - An efficient and recyclable organocatalyst for Michael addition to α,β-unsaturated ketones

(4) Muthyala, Manoj Kumar a Chhikara, Bhupender S b Parang, Keykavous b Kumar, Anil a

a BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE (India)

b UNIVERSITY OF RHODE ISLAND (United States)

Author keywords

, unsaturated ketones; Ionic liquid; Michael addition; Organocatalyst; Supported catalysis

Indexed keywords

1 ,5 ,7-TRIAZABICYCLO[4.4.0]DEC-5-ENE; ACTIVE METHYLENE COMPOUNDS; CHALCONES; MICHAEL ADDITIONS; ORGANOCATALYSTS; ROOM TEMPERATURE; SOLVENT FREE CONDITIONS; SUPPORTED CATALYSIS; THIOPHENOLS; UNSATURATED KETONES;

IONIC LIQUIDS; KETONES; UNSATURATED COMPOUNDS;

ADDITION REACTIONS;

EID: 84863279337 PISSN: 00084042 EISSN: None Source Type: Journal
DOI: 10.1139/v11-162 Document Type: Article

Times cited : (8)

References (50)

1
- 6044269452
- In the golden age of organocatalysis
- DOI 10.1002/anie.200400650
- Dalko P. I. Moisan L. Angew. Chem. Int. Ed. 2004, 43 (39), 5138. 10.1002/anie.200400650 (Pubitemid 39382534)
- (2004) Angewandte Chemie - International Edition , vol.43 , Issue.39 , pp. 5138-5175
- Dalko, P.I.¹ Moisan, L.²

2
- 48849094479
- 10.1002/anie.200704684
- Dondoni A. Massi A. Angew. Chem. Int. Ed. 2008, 47 (25), 4638. 10.1002/anie.200704684
- (2008) Angew. Chem. Int. Ed. , vol.47 , Issue.25 , pp. 4638
- Dondoni, A.¹ Massi, A.²

3
- 48649106016
- 10.1002/asia.200700415
- Yu X. Wang W. Chem. Asian J. 2008, 3 (3), 516. 10.1002/asia.200700415
- (2008) Chem. Asian J. , vol.3 , Issue.3 , pp. 516
- Yu, X.¹ Wang, W.²

4
- 38349142750
- 10.1021/cr078412e
- List B. Chem. Rev. 2007, 107 (12), 5413. 10.1021/cr078412e
- (2007) Chem. Rev. , vol.107 , Issue.12 , pp. 5413
- List, B.¹

5
- 84856804248
- Wiley-VCH: Weinheim, Germany
- Wasserscheid, P.; Welton, T. Ionic Liquids in Synthesis; Wiley-VCH: Weinheim, Germany, 2008.
- (2008) Ionic Liquids in Synthesis
- Wasserscheid, P.¹ Welton, T.²

6
- 12344296667
- Chemical and biochemical transformations in ionic liquids
- DOI 10.1016/j.tet.2004.10.070, PII S0040402004017867
- Jain N. Kumar A. Chauhan S. Chauhan S. M. S. Tetrahedron 2005, 61 (5), 1015. 10.1016/j.tet.2004.10.070 (Pubitemid 40126710)
- (2005) Tetrahedron , vol.61 , Issue.5 , pp. 1015-1060
- Jain, N.¹ Kumar, A.² Chauhan, S.³ Chauhan, S.M.S.⁴

7
- 79955884563
- 10.1021/cr1003248
- Hallett J. P. Welton T. Chem. Rev. 2011, 111 (5), 3508. 10.1021/cr1003248
- (2011) Chem. Rev. , vol.111 , Issue.5 , pp. 3508
- Hallett, J.P.¹ Welton, T.²

8
- 0035824303
- 10.1039/b107270f
- Sheldon R. Chem. Commun. (Camb.) 2001 (23), 2399. 10.1039/b107270f
- (2001) Chem. Commun. (Camb.) , Issue.23 , pp. 2399
- Sheldon, R.¹

9
- 25444492607
- Microwave-assisted preparation of 1-butyl-3-methylimidazolium tetrachlorogallate and its catalytic use in acetal formation under mild conditions
- DOI 10.1016/j.tetlet.2005.08.059, PII S0040403905017922
- Kim Y. J. Varma R. S. Tetrahedron Lett. 2005, 46 (43), 7447. 10.1016/j.tetlet.2005.08.059 (Pubitemid 41365871)
- (2005) Tetrahedron Letters , vol.46 , Issue.43 , pp. 7447-7449
- Yong, J.K.¹ Varma, R.S.²

10
- 26844464592
- 4 under microwave irradiation
- DOI 10.1021/jo051373r
- Ranu B. C. Jana R. J. Org. Chem. 2005, 70 (21), 8621. 10.1021/jo051373r (Pubitemid 41457036)
- (2005) Journal of Organic Chemistry , vol.70 , Issue.21 , pp. 8621-8624
- Ranu, B.C.¹ Jana, R.²

11
- 33846248338
- 10.1021/ar030252f
- Miao W. Chan T. H. Acc. Chem. Res. 2006, 39 (12), 897. 10.1021/ar030252f
- (2006) Acc. Chem. Res. , vol.39 , Issue.12 , pp. 897
- Miao, W.¹ Chan, T.H.²

12
- 33644806022
- Functionalized imidazolium salts for task-specific ionic liquids and their applications
- DOI 10.1039/b514140k
- Lee S. Chem. Commun. (Camb.) 2006 (10), 1049. 10.1039/b514140k (Pubitemid 43348519)
- (2006) Chemical Communications , Issue.10 , pp. 1049-1063
- Lee, S.-G.¹

13
- 0035819377
- 10.1039/b008041l
- Visser A. E. Swatloski R. P. Reichert W. M. Mayton R. Sheff S. Wierzbicki A. Davis J. H. Jr. Rogers R. D. Chem. Commun. (Camb.) 2001 (1), 135. 10.1039/b008041l
- (2001) Chem. Commun. (Camb.) , Issue.1 , pp. 135
- Visser, A.E.¹ Swatloski, R.P.² Reichert, W.M.³ Mayton, R.⁴ Sheff, S.⁵ Wierzbicki, A.⁶ Davis, Jr.J.H.⁷ Rogers, R.D.⁸

14
- 0037065704
- 2 capture by a task-specific ionic liquid
- DOI 10.1021/ja017593d
- Bates E. D. Mayton R. D. Ntai I. Davis J. H. J. Am. Chem. Soc. 2002, 124 (6), 926. 10.1021/ja017593d (Pubitemid 34130976)
- (2002) Journal of the American Chemical Society , vol.124 , Issue.6 , pp. 926-927
- Bates, E.D.¹ Mayton, R.D.² Ntai, I.³ Davis Jr., J.H.⁴

15
- 22244486653
- 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
- DOI 10.1021/ol051004h
- Ranu B. C. Banerjee S. Org. Lett. 2005, 7 (14), 3049. 10.1021/ol051004h (Pubitemid 40992628)
- (2005) Organic Letters , vol.7 , Issue.14 , pp. 3049-3052
- Ranu, B.C.¹ Banerjee, S.²

16
- 0042709622
- An ionic liquid-supported ruthenium carbene complex: A robust and recyclable catalyst for ring-closing olefin metathesis in ionic liquids
- DOI 10.1021/ja021484x
- Audic N. Clavier H. Mauduit M. Guillemin J.-C. J. Am. Chem. Soc. 2003, 125 (31), 9248. 10.1021/ja021484x (Pubitemid 36936018)
- (2003) Journal of the American Chemical Society , vol.125 , Issue.31 , pp. 9248-9249
- Audic, N.¹ Clavier, H.² Mauduit, M.³ Guillemin, J.-C.⁴

17
- 38349023020
- 10.1016/j.tetlet.2007.12.044
- Siyutkin D. E. Kucherenko A. S. Struchkova M. I. Zlotin S. G. Tetrahedron Lett. 2008, 49 (7), 1212. 10.1016/j.tetlet.2007.12.044
- (2008) Tetrahedron Lett. , vol.49 , Issue.7 , pp. 1212
- Siyutkin, D.E.¹ Kucherenko, A.S.² Struchkova, M.I.³ Zlotin, S.G.⁴

18
- 10044231966
- 10.1021/ja0463482
- Zhao D. Fei Z. Geldbach T. J. Scopelliti R. Dyson P. J. J. Am. Chem. Soc. 2004, 126 (48), 15876. 10.1021/ja0463482
- (2004) J. Am. Chem. Soc. , vol.126 , Issue.48 , pp. 15876
- Zhao, D.¹ Fei, Z.² Geldbach, T.J.³ Scopelliti, R.⁴ Dyson, P.J.⁵

19
- 15444371840
- Ionic liquid-immobilized quinuclidine-catalyzed Morita-Baylis-Hillman reactions
- DOI 10.1021/jo048391d
- Mi X. Luo S. Cheng J.-P. J. Org. Chem. 2005, 70 (6), 2338. 10.1021/jo048391d (Pubitemid 40395178)
- (2005) Journal of Organic Chemistry , vol.70 , Issue.6 , pp. 2338-2341
- Mi, X.¹ Luo, S.² Cheng, J.-P.³

20
- 7044222418
- An ionic liquid-coordinated palladium complex: A highly efficient and recyclable catalyst for the Heck reaction
- DOI 10.1021/ol048327i
- Xiao J.-C. Twamley B. Shreeve J. M. Org. Lett. 2004, 6 (21), 3845. 10.1021/ol048327i (Pubitemid 39421959)
- (2004) Organic Letters , vol.6 , Issue.21 , pp. 3845-3847
- Xiao, J.-C.¹ Twamley, B.² Shreeve, J.M.³

21
- 0043031400
- Olefin metathesis in the ionic liquid 1-butyl-3-methylimidazolium hexafiuorophosphate using a recyclable Ru catalyst: Remarkable effect of a designer ionic tag
- DOI 10.1002/anie.200351222
- Yao Q. Zhang Y. Angew. Chem. Int. Ed. 2003, 42 (29), 3395. 10.1002/anie.200351222 (Pubitemid 36975336)
- (2003) Angewandte Chemie - International Edition , vol.42 , Issue.29 , pp. 3395-3398
- Yao, Q.¹ Zhang, Y.²

22
- 58149352252
- 10.1016/j.tet.2008.12.045
- Siyutkin D. E. Kucherenko A. S. Zlotin S. G. Tetrahedron 2009, 65 (7), 1366. 10.1016/j.tet.2008.12.045
- (2009) Tetrahedron , vol.65 , Issue.7 , pp. 1366
- Siyutkin, D.E.¹ Kucherenko, A.S.² Zlotin, S.G.³

23
- 33748281160
- Ionic-liquid-supported organocatalyst: Efficient and recyclable ionic-liquid-anchored proline for asymmetric aldol reaction
- DOI 10.1002/adsc.200606059
- Miao W. Chan T. H. Adv. Synth. Catal. 2006, 348 (12-13), 1711. 10.1002/adsc.200606059 (Pubitemid 44318770)
- (2006) Advanced Synthesis and Catalysis , vol.348 , Issue.12-13 , pp. 1711-1718
- Miao, W.¹ Chan, T.H.²

24
- 33746216402
- Functionalized chiral ionic liquids as highly efficient asymmetric organocatalysts for michael addition to nitroolefins
- DOI 10.1002/anie.200600048
- Luo S. Mi X. Zhang L. Liu L. Xu H. Cheng J.-P. Angew. Chem. Int. Ed. 2006, 45 (19), 3093-3097. 10.1002/anie.200600048 (Pubitemid 44099025)
- (2006) Angewandte Chemie - International Edition , vol.45 , Issue.19 , pp. 3093-3097
- Luo, S.¹ Mi, X.² Zhang, L.³ Liu, S.⁴ Xu, H.⁵ Cheng, J.-P.⁶

25
- 36648999792
- Functionalized chiral ionic liquid catalyzed enantioselective desymmetrizations of prochiral ketones via asymmetric Michael addition reaction
- DOI 10.1021/jo7020357
- Luo S. Zhang L. Mi X. Qiao Y. Cheng J.-P. J. Org. Chem. 2007, 72 (24), 9350. 10.1021/jo7020357 (Pubitemid 350195810)
- (2007) Journal of Organic Chemistry , vol.72 , Issue.24 , pp. 9350-9352
- Luo, S.¹ Zhang, L.² Mi, X.³ Qiao, Y.⁴ Cheng, J.-P.⁵

26
- 34547357512
- 10.1039/b702081c
- Ni B. K. Zhang Q. Y. Headley A. D. Green Chem. 2007, 9 (7), 737. 10.1039/b702081c
- (2007) Green Chem. , vol.9 , Issue.7 , pp. 737
- Ni, B.K.¹ Zhang, Q.Y.² Headley, A.D.³

27
- 38349049059
- 10.1016/j.tetlet.2007.12.024
- Ni B. K. Zhang Q. Y. Headley A. D. Tetrahedron Lett. 2008, 49 (7), 1249-1252. 10.1016/j.tetlet.2007.12.024
- (2008) Tetrahedron Lett. , vol.49 , Issue.7 , pp. 1249-1252
- Ni, B.K.¹ Zhang, Q.Y.² Headley, A.D.³

28
- 45649083198
- 10.1016/j.tet.2008.05.039
- Li P. Wang L. Zhang Y. Wang G. Tetrahedron 2008, 64 (32), 7633. 10.1016/j.tet.2008.05.039
- (2008) Tetrahedron , vol.64 , Issue.32 , pp. 7633
- Li, P.¹ Wang, L.² Zhang, Y.³ Wang, G.⁴

29
- 34748882366
- Ionic-liquid-supported organocatalyst for the enantioselective Michael addition of ketones to nitroolefins
- DOI 10.1016/j.tetasy.2007.08.029, PII S0957416607006362
- Wu L.-Y. Yan Z.-Y. Xie Y.-X. Niu Y.-N. Liang Y.-M. Tetrahedron Asymmetry 2007, 18 (17), 2086. 10.1016/j.tetasy.2007.08.029 (Pubitemid 47484427)
- (2007) Tetrahedron Asymmetry , vol.18 , Issue.17 , pp. 2086-2090
- Wu, L.-Y.¹ Yan, Z.-Y.² Xie, Y.-X.³ Niu, Y.-N.⁴ Liang, Y.-M.⁵

30
- 42749087995
- 10.1016/j.tet.2008.03.073
- Zhang Q. Ni B. Headley A. D. Tetrahedron 2008, 64 (22), 5091. 10.1016/j.tet.2008.03.073
- (2008) Tetrahedron , vol.64 , Issue.22 , pp. 5091
- Zhang, Q.¹ Ni, B.² Headley, A.D.³

31
- 64349100404
- 10.1021/ol900003e
- Ni B. K. Zhang Q. Dhungana K. Headley A. D. Org. Lett. 2009, 11 (4), 1037. 10.1021/ol900003e
- (2009) Org. Lett. , vol.11 , Issue.4 , pp. 1037
- Ni, B.K.¹ Zhang, Q.² Dhungana, K.³ Headley, A.D.⁴

32
- 48949121232
- 10.1002/ejoc.200701037
- Li P. Wang P. Wang M. Zhang Y. Eur. J. Org. Chem. 2008, 2008 (7), 1157. 10.1002/ejoc.200701037
- (2008) Eur. J. Org. Chem. , vol.2008 , Issue.7 , pp. 1157
- Li, P.¹ Wang, P.² Wang, M.³ Zhang, Y.⁴

33
- 0000406890
- 10.1016/0022-2860(94)08427-J
- Schroeder G. Brzezinski B. Podebski D. Grech E. J. Mol. Struct. 1995, 344 (1-2), 77. 10.1016/0022-2860(94)08427-J
- (1995) J. Mol. Struct. , vol.344 , Issue.12 , pp. 77
- Schroeder, G.¹ Brzezinski, B.² Podebski, D.³ Grech, E.⁴

34
- 27744501832
- 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) catalyzed Michael reactions
- DOI 10.1016/j.tetlet.2005.08.010
- Ye W. Xu J. Tan C.-T. Tan C.-H. Tetrahedron Lett. 2005, 46 (40), 6875. 10.1016/j.tetlet.2005.08.010 (Pubitemid 41583408)
- (2005) Tetrahedron Letters , vol.46 , Issue.40 , pp. 6875-6878
- Ye, W.¹ Xu, J.² Tan, C.-T.³ Tan, C.-H.⁴

35
- 2442640224
- Utilization of nonionic bases in water as a highly efficient organocatalytic system for Michael addition of β-ketoesters
- DOI 10.1081/SCC-120030703
- Bensa D. Rodriguez J. Synth. Commun. 2004, 34 (8), 1515. 10.1081/SCC-120030703 (Pubitemid 38669814)
- (2004) Synthetic Communications , vol.34 , Issue.8 , pp. 1515-1533
- Bensa, D.¹ Rodriguez, J.²

36
- 78650228720
- 10.1016/j.tetlet.2010.11.032
- Cota I. Medina F. Sueiras J. E. Tichit D. Tetrahedron Lett. 2011, 52 (3), 385. 10.1016/j.tetlet.2010.11.032
- (2011) Tetrahedron Lett. , vol.52 , Issue.3 , pp. 385
- Cota, I.¹ Medina, F.² Sueiras, J.E.³ Tichit, D.⁴

37
- 67649859509
- 10.1039/b901940e
- Coles M. P. Chem. Commun. (Camb.) 2009 (25), 3659. 10.1039/b901940e
- (2009) Chem. Commun. (Camb.) , Issue.25 , pp. 3659
- Coles, M.P.¹

38
- 0026985233
- 10.1080/00222339208052124
- Iijima K. Fukuda W. Tomoi M. J. Macromol. Sci. Pure Appl. Chem. 1992, A29 (3), 249. 10.1080/00222339208052124
- (1992) J. Macromol. Sci. Pure Appl. Chem. , vol.29 A , Issue.3 , pp. 249
- Iijima, K.¹ Fukuda, W.² Tomoi, M.³

39
- 0000833799
- 10.1002/macp.1984.021851007
- Tomoi M. Kato Y. Kakiuchi H. Makromol. Chem. 1984, 185 (10), 2117. 10.1002/macp.1984.021851007
- (1984) Makromol. Chem. , vol.185 , Issue.10 , pp. 2117
- Tomoi, M.¹ Kato, Y.² Kakiuchi, H.³

40
- 0000926785
- 10.1002/macp.1985.021861207
- Tomoi M. Watanabe T. Suzuki T. Kakiuchi H. Makromol. Chem. 1985, 186 (12), 2473. 10.1002/macp.1985.021861207
- (1985) Makromol. Chem. , vol.186 , Issue.12 , pp. 2473
- Tomoi, M.¹ Watanabe, T.² Suzuki, T.³ Kakiuchi, H.⁴

41
- 33747039253
- 2-TBD as new heterogeneous catalyst for the nef conversion of secondary nitroalkanes under neat conditions
- DOI 10.1055/s-2006-947358
- Ballini R. Fiorini D. Maggi R. Oro C. Palmieri A. Sartori G. Synlett 2006, 2006 (12), 1849. 10.1055/s-2006-947358 (Pubitemid 44214806)
- (2006) Synlett , Issue.12 , pp. 1849-1850
- Ballini, R.¹ Fiorini, D.² Maggi, R.³ Oro, C.⁴ Palmieri, A.⁵ Sartori, G.⁶

42
- 0030767571
- Polymer supported bases in combinatorial chemistry: Synthesis of aryl ethers from phenols and alkyl halides and aryl halides
- DOI 10.1016/S0040-4039(97)01782-6, PII S0040403997017826
- Xu W. Mohan R. Morrissey M. M. Tetrahedron Lett. 1997, 38 (42), 7337. 10.1016/S0040-4039(97)01782-6 (Pubitemid 27435124)
- (1997) Tetrahedron Letters , vol.38 , Issue.42 , pp. 7337-7340
- Xu, W.¹ Mohan, R.² Morrissey, M.M.³

43
- 11144351845
- Polystyryl-supported TBD as an efficient and reusable catalyst under solvent-free conditions
- DOI 10.1039/b409808k
- Fringuelli F. Pizzo F. Vittoriani C. Vaccaro L. Chem. Commun. (Camb.) 2004 (23), 2756. 10.1039/b409808k (Pubitemid 40029569)
- (2004) Chemical Communications , Issue.23 , pp. 2756-2757
- Fringuelli, F.¹ Pizzo, F.² Vittoriani, C.³ Vaccaro, L.⁴

44
- 0039945438
- 10.1002/anie.199726611
- Subba Rao Y. V. De Vos D. E. Jacobs P. A. Angew. Chem. Int. Ed. Engl. 1997, 36 (23), 2661. 10.1002/anie.199726611
- (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , Issue.23 , pp. 2661
- Subba Rao, Y.V.¹ De Vos, D.E.² Jacobs, P.A.³

45
- 0037131742
- MCM-41-TBD as a new, efficient, supported heterogeneous catalyst for the synthesis of thioureas
- DOI 10.1016/S0040-4039(02)02100-7, PII S0040403902021007
- Ballini R. Bosica G. Fiorini D. Maggi R. Righi P. Sartori G. Sartorio R. Tetrahedron Lett. 2002, 43 (47), 8445. 10.1016/S0040-4039(02)02100-7 (Pubitemid 35232644)
- (2002) Tetrahedron Letters , vol.43 , Issue.47 , pp. 8445-8447
- Ballini, R.¹ Bosica, G.² Fiorini, D.³ Maggi, R.⁴ Righi, P.⁵ Sartori, G.⁶ Sartorio, R.⁷

46
- 0037565118
- Convenient preparation of aryl ether derivatives using a sequence of functionalized polymers
- DOI 10.1016/S0040-4039(03)01117-1
- Lizarzaburu M. E. Shuttleworth S. J. Tetrahedron Lett. 2003, 44 (26), 4873. 10.1016/S0040-4039(03)01117-1 (Pubitemid 36694257)
- (2003) Tetrahedron Letters , vol.44 , Issue.26 , pp. 4873-4876
- Lizarzaburu, M.E.¹ Shuttleworth, S.J.²

47
- 0000767774
- 10.1039/a904384e
- Habermann J. Ley S. V. Smits R. J. Chem. Soc., Perkin Trans. 1 1999, (17): 2421. 10.1039/a904384e
- (1999) J. Chem. Soc., Perkin Trans. 1 , Issue.17 , pp. 2421
- Habermann, J.¹ Ley, S.V.² Smits, R.³

48
- 0000196260
- 10.1039/a905616e
- Habermann J. Ley S. V. Scicinski J. J. Scott J. S. Smits R. Thomas A. W. J. Chem. Soc., Perkin Trans. 1 1999, (17): 2425. 10.1039/a905616e
- (1999) J. Chem. Soc., Perkin Trans. 1 , Issue.17 , pp. 2425
- Habermann, J.¹ Ley, S.V.² Scicinski, J.J.³ Scott, J.S.⁴ Smits, R.⁵ Thomas, A.W.⁶

49
- 10144250310
- 10.1016/1381-1169(96)00014-3
- Schuchardt U. Vargas R. M. Gelbard G. J. Mol. Catal. 1996, 109 (1), 37. 10.1016/1381-1169(96)00014-3
- (1996) J. Mol. Catal. , vol.109 , Issue.1 , pp. 37
- Schuchardt, U.¹ Vargas, R.M.² Gelbard, G.³

50
- 11844304177
- (1).
- Chhikara B. S. Tehlan S. Kumar A. Synlett 2005 (1), 63.
- (2005) Synlett , pp. 63
- Chhikara, B.S.¹ Tehlan, S.² Kumar, A.³

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