Supported gold nanoparticles as heterogeneous catalysts for C-C coupling reactions

Gold Catalysis: Preparation, Characterization and Applications

Volumn , Issue , 2015, Pages 389-414

  Primo, Ana ^a   García, Hermenegildo ^a  

^a INSTITUTO DE TECNOLOGÍA QUÍMICA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

C-C COUPLING REACTIONS; HETEROGENEOUS CATALYST; SUPPORTED GOLD;

EID: 85009673231     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.4032/9789814669290     Document Type: Chapter

References (40)

1. Li, C.J. (1993). Organic reactions in aqueous media-with a focus on carbon-carbon bond formation, Chem. Rev., 93, pp. 2023-2035.
2. Smith, M.B., and March, J. (2007). March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (Wiley & Sons, New Jersey).
3. Maruyama, K., and Katagiri, T. (1989). Mechanism of the Grignard reaction, J. Phys. Org. Chem., 2, pp. 205-213.
4. Ritleng, V., Sirlin, C., and Pfeffer, M. (2002). Ru-, Rh-, and Pd-catalyzed CC bond formation involving C-H activation and addition on unsaturated substrates: reactions and mechanistic aspects, Chem. Rev., 102, pp. 1731-1769.
5. Kalyani, D., Deprez, N.R., Desai, L.V., and Sanford, M.S. (2005). Oxidative C-H activation/C-C bond forming reactions: synthetic scope and mechanistic insights, J. Am. Chem. Soc., 127, pp. 7330-7331.
6. Hartwig, J.F. (1998). Carbon-heteroatom bond-forming reductive eliminations of amines, ethers, and sulfides, Acc. Chem. Res., 31, pp. 852-860.
7. Astruc, D., Lu, F., and Ruiz Aranzaes, J. (2005). Nanoparticles as recyclable catalysts: the frontier between homogeneous and heterogeneous catalysis, Angew. Chem., Int. Ed., 44, pp. 7852-7872.
8. Corma, A., and Garcia, H. (2006). Silica-bound homogeneous catalysts as recoverable and reusable catalysts in organic synthesis, Adv. Synth. Catal., 348, pp. 1391-1412.
9. Wolfe, J.P., Singer, R.A., Yang, B.H., and Buchwald, S.L. (1999). Highly active palladium catalysts for Suzuki coupling reactions, J. Am. Chem. Soc., 121, pp. 9550-9561.
10. Old, D.W., Wolfe, J.P., and Buchwald, S.L. (1998). A highly active catalyst for palladium-catalyzed cross-coupling reactions: room-temperature Suzuki couplings and amination of unactivated aryl chlorides, J. Am. Chem. Soc., 120, pp. 9722-9723.
11. De Vos, D.E., Dams, M., Sels, B.F., and Jacobs, P.A. (2002). Ordered mesoporous and microporous molecular sieves functionalized with transition metal complexes as catalysts for selective organic transformations, Chem. Rev., 102, pp. 3615-3640.
12. Abad, A., Almela, C., Corma, A., and Garcia, H. (2006). Efficient chemoselective alcohol oxidation using oxygen as oxidant. Superior performance of gold over palladium catalysts, Tetrahedron, 62, pp. 6666-6672.
13. Haruta, M., Yamada, N., Kobayashi, T., and Iijima, S. (1989). Gold catalysts prepared by coprecipitation for low-temperature oxidation of hydrogen and of carbon monoxide, J. Catal., 115, pp. 301-309.
14. Corma, A., and Garcia, H. (2008). Supported gold nanoparticles as catalysts for organic reactions, Chem. Rev., 37, pp. 2096-2126.
15. Haruta, M. (2002). Catalysis of Gold Nanoparticles Deposited on Metal Oxides, CATECH, 6, pp. 102-115 (Springer).
16. 7 at room temperature, Science, 338, pp. 1452-1455.
17. 2 catalysts for the water-gas shift reaction, Angew. Chem., Int. Ed., 47, pp. 2884-2887.
18. Corma, A., and Domine, M.E. (2005). Gold supported on a mesoporous CeO2 matrix as an efficient catalyst in the selective aerobic oxidation of aldehydes in the liquid phase, Chem. Commun., 32, pp. 4042-4044.
19. 2, J. Am. Chem. Soc., 127, pp. 3286-3287.
20. 2 increases the activity of Au for CO oxidation by two orders of magnitude, Angew. Chem., Int. Ed., 43, pp. 2538-2540.
21. Abad, A., Concepción, P., Corma, A., and Garcia, H. (2005). A collaborative effect between gold and a support induces the selective oxidation of alcohols, Angew. Chem., Int. Ed., 44, pp. 4066-4069.
22. Carretin, S., Blanco, M.C., Corma, A., and Hashmi, A.S.K. (2006). Heterogeneous gold-catalysed synthesis of phenols, Adv. Synth. Catal., 348, pp. 1283-1288.
23. Carrettin, S., Guzman, J., and Corma, A. (2005). Supported gold catalyzes the homocoupling of phenylboronic acid with high conversion and selectivity, Angew. Chem., Int. Ed., 44, pp. 2242-2245.
24. Zhou, X., Liu, G., Yu, J., and Fan, W. (2012). Surface plasmon resonance-mediated photocatalysis by noble metal-based composites under visible light, J. Mater. Chem., 22, pp. 21337-21354.
25. Link, S., and El-Sayed, M.A. (1999). Size and temperature dependence of the plasmon absorption of colloidal gold nanoparticles, J. Phys. Chem. B, 103, pp. 4212-4217.
26. Abad, A., Corma, A., and Garcia, H. (2007). Bridging the gap between homogeneous and heterogeneous gold catalysis: supported gold nanoparticles as heterogeneous catalysts for the benzannulation reaction, Top. Catal., 44, pp. 237-243.
27. Hallett-Tapley, G.L., D'Alfonso, C., Pacioni, N.L., McTiernan, C.D., González Béjar, M., Lanzalunga, O., Alarcon, E.I., and Scaiano, J.C. (2013). Gold nanoparticle catalysis of the cis-trans isomerization of azobenzene, Chem. Commun., 49, pp. 10073-10075.
28. Fasciani, C., Bueno Alejo, C.J., Grenier, M., Netto-Ferreira, J.C., and Scaiano, J.C. (2011). High-Temperature organic reactions at room temperature using plasmon excitation: decomposition of dicumyl peroxide, Org. Lett., 13, pp. 204-207.
29. Alvaro, M., Aprile, C., Ferrer, B., Sastre, F., and Garcia, H. (2009). Photochemistry of gold nanoparticles functionalized with an iron(II) terpyridine complex. An integrated visible light photocatalyst for hydrogen generation, Dalton Trans., 36, pp. 7437-7444.
30. Wang, F., Li, C.C.H., Jiang, R., Sun, L.D., Li, Q., Wang, J., Yu, J.C., and Yan, C.H. (2013). Plasmonic harvesting of light energy for Suzuki coupling reactions, J. Am. Chem. Soc., 135, pp. 5588-5601.
31. Dupont, J., and Scholten, J.D. (2010). On the structural and surface properties of transition-metal nanoparticles in ionic liquids, Chem. Soc. Rev., 39, pp. 1780-1804.
32. Sempere, D., Navalon, S., Dancíková, M., Alvaro, M., and Garcia, H. (2013). Influence of pretreatments on commercial diamond nanoparticles on the photocatalytic activity of supported gold nanoparticles under natural Sunlight irradiation, Appl. Catal. B: Environ., 142-143, pp. 259-267.
33. Navalon, S., Martin, R., Alvaro, M., and Garcia, H. (2010). Gold on diamond nanoparticles as a highly efficient Fenton catalyst, Angew. Chem., Int. Ed., 49, pp. 8403-8407.
34. Boronat, M., Concepción, P., and Corma, A. (2009). Unravelling the nature of gold surface sites by combining IR spectroscopy and DFT calculations, implications in catalysis, J. Phys. Chem. C, 113, pp. 16772-16784.
35. Primo, A., and Quignard, F. (2010). Chitosan as efficient porous support for dispersion of highly active gold nanoparticles: design of hybrid catalyst for carbon-carbon bond formation, Chem. Commun., 46, pp. 5593-5595.
36. Lauterbach, T., Livendahl, M., Rosellón, A., Espinet, P., and Echavarren, A.M. (2010). Unlikeliness of Pd-free gold(I)-catalyzed Sonogashira coupling reactions, Org. Lett., 12, pp. 3006-3009.
37. González-Arellano, C., Abad, A., Corma, A., Garcia, H., Iglesias, M., and Sánchez, F. (2007). Catalysis by gold(I) and gold(III): a parallelism between homo- and heterogeneous catalysts for copper-free Sonogashira cross-coupling reactions, Angew. Chem., Int. Ed., 119, pp. 1558-1560.
38. 3, Angew. Chem., Int. Ed., 48, pp. 5586-5587.
39. Thomé, I., Nijs, A., and Bolm, C. (2012). Trace metal impurities in catalysis, Chem. Soc. Rev., 41, pp. 979-987.
40. Corma, A., Juárez, R., Boronat, M., Sánchez, F., Iglesias, M., and Garcia, H. (2011). Gold catalyzes the Sonogashira coupling reaction without the requirement of palladium impurities, Chem. Commun., 47, pp. 1446-1448.