Ionic liquid-supported aldehyde: A highly efficient scavenger for primary amines

ACS Combinatorial Science

Volumn 14, Issue 1, 2012, Pages 5-9

  Muthayala, Manoj Kumar ^a   Kumar, Anil ^a  

^a BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE   (India)

Author keywords

functionalized ionic liquid; Ionic liquid; reductive amination; scavenger; secondary amines

Indexed keywords

ALDEHYDE; AMINE; IMINE; IONIC LIQUID;

AMINATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALDEHYDES; AMINATION; AMINES; COMBINATORIAL CHEMISTRY TECHNIQUES; IMINES; IONIC LIQUIDS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 84862908688     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co200151n     Document Type: Article

References (30)

1. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Solid-phase organic reactions ii: A review of the literature nov 95-nov 96 Tetrahedron 1997, 53, 5643
2. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Solid-phase organic reactions: A review of the recent literature Tetrahedron 1996, 52, 4527
3. Hodge, P. Synthesis of organic compounds using polymer-supported reagents, catalysts, and/or scavengers in benchtop flow systems Ind. Eng. Chem. Res. 2005, 44, 8542-8553 (Pubitemid 41729317)
4. Baxendale, I. R.; Ley, S. V. Synthesis of the alkaloid natural products (+)-plicane and (-)-obliquine, using polymer-supported reagents and scavengers Ind. Eng. Chem. Res. 2005, 44, 8588-8592 (Pubitemid 41729323)
5. Azuaje, J.; Coelho, A.; Maatougui, A. E.; Blanco, J. M.; Sotelo, E. Supported p-toluenesulfonic acid as a highly robust and eco-friendly isocyanide scavenger ACS Comb. Sci. 2011, 13, 89-95
6. Falchi, A.; Taddei, M. Peg-dichlorotriazine (peg-dct): A new soluble polymer-supported scavenger for alcohols, thiols, phosphines, and phosphine oxides Org. Lett. 2000, 2, 3429-3431
7. 6] as a scavenger for the synthesis of amides Mol. Diversity 2011, 15, 109-113
8. Linclau, B.; Sing, A. K.; Curran, D. P. Organic-fluorous phase switches: A fluorous amine scavenger for purification in solution phase parallel synthesis J. Org. Chem. 1999, 64, 2835-2842
9. Lindsley, C. W.; Zhao, Z.; Leister, W. H. Fluorous-tethered quenching reagents for solution phase parallel synthesis Tetrahedron Lett. 2002, 43, 4225-4228 (Pubitemid 34603190)
10. Zhang, W.; Chen, C. H.-T.; Nagashima, T. Fluorous electrophilic scavengers for solution-phase parallel synthesis Tetrahedron Lett. 2003, 44, 2065-2068 (Pubitemid 36197752)
11. Ghanem, N.; Martinez, J.; Stien, D. A new high-loading water-soluble scavenger for anhydrides, acid chlorides and isocyanates Tetrahedron Lett. 2002, 43, 1693-1695 (Pubitemid 34169678)
12. Lin, C.-E.; Richardson, S. K.; Garvey, D. S. l -Cysteine as a water-soluble cation scavenger in the removal of the 2,4,6-trimethoxybenzyl group from thiols Tetrahedron Lett. 2002, 43, 4531-4533 (Pubitemid 34615862)
13. Jain, N.; Kumar, A.; Chauhan, S.; Chauhan, S. M. S. Chemical and biochemical transformations in ionic liquids Tetrahedron 2005, 61, 1015-1060 (Pubitemid 40126710)
14. Miao, W.; Chan, T. H. Ionic-liquid-supported synthesis: A novel liquid-phase strategy for organic synthesis Acc. Chem. Res. 2006, 39, 897-908
15. Kamal, A.; Chouhan, G. A task-specific ionic liquid [bmim]scn for the conversion of alkyl halides to alkyl thiocyanates at room temperature Tetrahedron Lett. 2005, 46, 1489-1491 (Pubitemid 40215050)
16. Visser, A. E.; Swatloski, R. P.; Reichert, W. M.; Mayton, R.; Sheff, S.; Wierzbicki, A.; Davis, J. J. H.; Rogers, R. D. Task-specific ionic liquids for the extraction of metal ions from aqueous solutions Chem. Commun., 2001, 135-136 (Pubitemid 32094851)
17. Lee, S. Functionalized imidazolium salts for task-specific ionic liquids and their applications Chem. Commun., 2006, 1049-1063 (Pubitemid 43348519)
18. Luo, S.; Mi, X.; Zhang, L.; Liu, S.; Xu, H.; Cheng, J.-P. Functionalized ionic liquids catalyzed direct aldol reactions Tetrahedron 2007, 63, 1923-1930 (Pubitemid 46136375)
19. 2 capture by a task-specific ionic liquid J. Am. Chem. Soc. 2002, 124, 926-927 (Pubitemid 34130976)
20. 3] mixtures: Promising media for the synthesis of aryl azides by snar J. Org. Chem. 2008, 73, 6224-6228
21. Song, G.; Cai, Y.; Peng, Y. Amino-functionalized ionic liquid as a nucleophilic scavenger in solution phase combinatorial synthesis J. Comb. Chem. 2005, 7, 561-566 (Pubitemid 41040493)
22. Cai, Y.; Liu, Y. A diol-functionalized ionic liquid: An efficient, simple, and recoverable "capture and release" reagent for aldehydes Monatsh. Chem. 2009, 140, 39-44
23. Cai, Y.; Zhang, Y.; Peng, Y.; Lu, F.; Huang, X.; Song, G. Carboxyl-functional ionic liquids as scavengers: Case studies on benzyl chloride, amines, and methanesulfonyl chloride J. Comb. Chem. 2006, 8, 636-638 (Pubitemid 44578614)
24. Maase, M.; Massonne, K. Biphasic acid scavenging utilizing ionic liquids: The first commercial process with ionic liquids. In Ionic Liquids IIIb: Fundamentals, Progress, Challenges, and Opportunities; American Chemical Society: Washington, DC, 2005; Vol. 902, pp 126-132.
25. Lei, M.; Tao, X.-L.; Wang, Y.-G. A practical, water-soluble, ionic scavenger for the solution-phase syntheses of amides Helv. Chim. Acta 2006, 89, 532-536
26. Kumar, A.; Rao, M. S.; Ahmad, I.; Khungar, B. A simple and facile synthesis of amidoalkyl naphthols catalyzed by yb(otf)3 in ionic liquids Can. J. Chem. 2009, 87, 714-719
27. 2 catalyzed by iron(III) porphyrins and horseradish peroxidase in ionic liquid Synlett, 2007, 411-414 (Pubitemid 46340216)
28. Kumar, A.; Ahmad, I.; Rao, M. S. Ytterbium(III) triflate catalyzed synthesis of calix[4]pyrroles in ionic liquids Can. J. Chem. 2008, 86, 899-902
29. Kumar, A.; Rao, M. S.; Ahmad, I.; Khungar, B. An efficient and simple one-pot synthesis of β-acetamido ketones catalyzed by ytterbium triflate in ionic liquid Aust. J. Chem. 2009, 62, 322-327
30. Guinó, M.; Brulé, E.; de Miguel, Y. R. Recycling and reuse of a polymer-supported scavenger for amine sequestration J. Comb. Chem. 2003, 5, 161-165 (Pubitemid 37123509)