Bifunctional Mesoporous Carbon Nitride: Highly Efficient Enzyme-like Catalyst for One-pot Deacetalization-Knoevenagel Reaction

Scientific Reports

Volumn 5, Issue , 2015, Pages

  Zhong, Lin ^a,b   Anand, Chokkalingam ^a   Lakhi, Kripal Singh ^a   Lawrence, Geoffrey ^a   Vinu, Ajayan ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

^b SICHUAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84938914100     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep12901     Document Type: Article

References (43)

1. Trost, B. M. The atom economy-a search for synthetic efficiency. Science 254, 1471-1477 (1991).
2. Clark, J. H. Green Chemistry: Challenges and opportunities. Green Chem. 1, 1-8 (1999).
3. Noyori, R. Editorial statement. Adv. Synth. Catal. 343, 1 (2001).
4. Mayer, S. F., Kroutil, W. & Kurt, F. Enzyme-initiated domino (cascade) reactions. Chem. Soc. Rev. 30, 332-339 (2001).
5. Perham, R. N. Swinging arms and swinging domains in multifunctional enzymes: Catalytic machines for multistep reactions. Annu. Rev. Biochem. 69, 961-1004 (2000).
6. Wasilke, J. C., Obrey, S. J., Baker, R. T. & Bazan, G. C. Concurrent tandem catalysis. Chem. Rev. 105, 1001-1020 (2005).
7. Bunce, R. A. Recent advance in the use of tandem reactions for organic-synthesis. Tetrahedron 51, 13103-13159 (1995).
8. Fogg, D. E. & dos Santos, E. N. Tandem catalysis: A taxonomy and illustrative review. Coord. Chem. Rev. 248, 2365-2379 (2004).
9. Tietze, L. F. Domino reactions in organic synthesis. Chem. Rev. 96, 115-136 (1996).
10. Voit, B. Sequential one-pot reactions using the concept of "Site isolation". Angew. Chem., Int. Ed. 45, 4238-4240 (2006).
11. Gladysz, J. A. Introduction: Recoverable catalysts and reagents-Perspective and prospective. Chem. Rev. 102, 3215-3216 (2002).
12. Gelman, F., Blum, J. & Avnir, D. Acids and bases in one pot while avoiding their mutual destruction. Angew. Chem., Int. Ed. 40, 3647-3649 (2001).
13. Motokura, K., Tada, M. & Iwasawa, Y. Layered Materials with Coexisting Acidic and Basic Sites for Catalytic One-Pot Reaction Sequences. J. Am. Chem. Soc. 131, 7944-7945 (2009).
14. Shylesh, S., Wagener, A., Seifert, A., Ernst, S. & Thiel, W. R. Mesoporous Organosilicas with Acidic Frameworks and Basic Sites in the Pores: An Approach to Cooperative Catalytic Reactions. Angew. Chem., Int. Ed. 49, 184-187 (2010).
15. Shiju, N. R., Alberts, A. H., Khalid, S., Brown, D. R. & Rothenberg, G. Mesoporous Silica with Site-Isolated Amine and Phosphotungstic Acid Groups: A Solid Catalyst with Tunable Antagonistic Functions for One-Pot Tandem Reactions. Angew. Chem., Int. Ed. 50, 9615-9619 (2011).
16. Jun, S. W. et al. One-pot synthesis of magnetically recyclable mesoporous silica supported acid-base catalysts for tandem reactions. Chem. Commun. 49, 7821-7823 (2013).
17. Climent, M. J., Corma, A., Iborra, S. & Sabater, M. J. Heterogeneous Catalysis for Tandem Reactions. ACS Catal. 4, 870-891 (2014).
18. Dhakshinamoorthy, A. & Garcia, H. Cascade Reactions Catalyzed by Metal Organic Frameworks. ChemSusChem 7, 2392-2410 (2014).
19. Vinu, A. et al. Preparation and characterization of well-ordered hexagonal mesoporous carbon nitride. Adv. Mater. 17, 1648-1652 (2005).
20. Wang, Y., Wang, X. & Antonietti, M. Polymeric Graphitic Carbon Nitride as a Heterogeneous Organocatalyst: From Photochemistry to Multipurpose Catalysis to Sustainable Chemistry. Angew. Chem., Int. Ed. 51, 68-89 (2012).
21. Wang, X. et al. A metal-free polymeric photocatalyst for hydrogen production from water under visible light. Nat. Mater. 8, 76-80 (2009).
22. Zheng, Y., Jiao, Y., Jaroniec, M., Jin, Y. & Qiao, S. Z. Nanostructured Metal-Free Electrochemical Catalysts for Highly Efficient Oxygen Reduction. Small 8, 3550-3566 (2012).
23. Li, Q. et al. Facile synthesis of porous carbon nitride spheres with hierarchical three-dimensional mesostructures for CO2 capture. Nano Research 3, 632-642 (2010).
24. Jin, X. et al. Highly Ordered Mesoporous Carbon Nitride Nanoparticles with High Nitrogen Content: A Metal-Free Basic Catalyst. Angew. Chem., Int. Ed. 48, 7884-7887 (2009).
25. Cheng, Y. C., Kaloni, T. P., Zhu, Z. Y. & Schwingenschlögl, U. Oxidation of graphene in ozone under ultraviolet light. Appl. Phys. Lett. 101, 073110-073114 (2012).
26. Huh, S. et al. UV/Ozone-Oxidized Large-Scale Graphene Platform with Large Chemical Enhancement in Surface-Enhanced Raman Scattering. ACS Nano 5, 9799-9806 (2011).
27. Leconte, N. et al. Damaging Graphene with Ozone Treatment: A Chemically Tunable Metal? Insulator Transition. ACS Nano 4, 4033-4038 (2010).
28. Jia, L. et al. Highly ordered macro-mesoporous carbon nitride film for selective detection of acidic/basic molecules. Chem. Commun. 50, 5976-5979 (2014).
29. Biniak, S., Szymanski, G., Siedlewski, J. & Swiatkowski, A. The characterization of activated carbons with oxygen and nitrogen surface groups. Carbon 35, 1799-1810 (1997).
30. Khabashesku, V. N., Zimmerman, J. L. & Margrave, J. L. Powder Synthesis and Characterization of Amorphous Carbon Nitride. Chem. Mater. 12, 3264-3270 (2000).
31. Hellgren, N. et al. Electronic structure of carbon nitride thin films studied by X-ray spectroscopy techniques. Thin Solid Films 471, 19-34 (2005).
32. Damjanovic, L. & Auroux, A. Zeolite Characterization and Catalysis: A Tutorial (eds Chester, Arthur W. & Derouane, E. G.) 107-167 (Springer 2010).
33. Fujita, S.-I. et al. Mesoporous smectites incorporated with alkali metal cations as solid base catalysts. Applied Catalysis a-General 313, 151-159 (2006).
34. Mane, G. P. et al. Preparation of Highly Ordered Nitrogen-Containing Mesoporous Carbon from a Gelatin Biomolecule and its Excellent Sensing of Acetic Acid. Adv. Funct. Mater. 22, 3596-3604 (2012).
35. Vinu, A. Two-dimensional hexagonally-ordered mesoporous carbon nitrides with tunable pore diameter, surface area and nitrogen content. Adv. Funct. Mater. 18, 816-827 (2008).
36. Hennig, M., Darimont, B. D., Jansonius, J. N. & Kirschner, K. The catalytic mechanism of indole-3-glycerol phosphate syntase: Crystal structures of complexes of the enzyme from Sulfolobus solfataricus with substrate analogue, substrate, and product. J. Mol. Biol. 319, 757-766 (2002).
37. Debler, E. W. et al. Structural origins of efficient proton abstraction from carbon by a catalytic antibody. Proc. Natl. Acad. Sci. USA. 102, 4984-4989 (2005).
38. Notestein, J. M. & Katz, A. Enhancing heterogeneous catalysis through cooperative hybrid organic-inorganic interfaces. Chemistry-a European Journal 12, 3954-3965 (2006).
39. Robinson, M. W. C. & Graham, A. E. Mesoporous aluminosilicate promoted protection and deprotection of carbonyl compounds. Tetrahedron Lett. 48, 4727-4731 (2007).
40. Gautier, E. C. L., Graham, A. E., McKillop, A., Standen, S. P. & Taylor, R. J. K. Acetal and ketal deprotection using montmorillonite K10: The first synthesis of syn-4,8-dioxatricyclo 5.1.0.0(3,5)-2,6-octanedione. Tetrahedron Lett. 38, 1881-1884 (1997).
41. Park, J. et al. A versatile metal-organic framework for carbon dioxide capture and cooperative catalysis. Chem. Commun. 48, 9995-9997 (2012).
42. Figueras, F., Kantam, M. L. & Choudary, B. M. Solid base catalysts in organic synthesis. Curr. Org. Chem. 10, 1627-1637 (2006).
43. Krishnan, G. R. & Sreekumar, K. First example of organocatalysis by polystyrene-supported PAMAM dendrimers: Highly efficient and reusable catalyst for Knoevenagel condensations. Eur. J. Org. Chem. 2008, 4763-4768 (2008).