Hexagonal Mesoporous Silica-Supported Copper Oxide (CuO/HMS) Catalyst: Synthesis of Primary Amides from Aldehydes in Aqueous Medium

. 2017 Mar ; 82 (3) : 467-473.

Status PubMed-not-MEDLINE Jazyk angličtina Země Německo Médium print

Typ dokumentu časopisecké články

Perzistentní odkaz   https://www.medvik.cz/link/pmid31962015

Hexagonal mesoporous silica (HMS)-supported copper oxides (CuO/HMS) have been prepared by a sol-gel method and characterized by X-ray diffraction, FTIR spectroscopy, transmission electron microscopy, N2 sorption, inductively coupled plasma (ICP), X-ray photoelectron spectroscopy (XPS), H2 temperature-programed reduction (TPR), NH3 temperature-programed desorption (TPD), and high-resolution (HR)-TEM techniques. An analysis of these results revealed a mesoporous material system with a high surface area (974 m2 g-1 ) and uniform pore-size distribution. The catalytic efficacy of CuO on the HMS support with varying Cu loadings (1, 3, 5, 10, and 15 wt %) was investigated for the transformation of aldehydes to primary amides; 3 wt % CuO/HMS exhibited good catalytic performance with good to excellent yields of amides (60-92 %) in benign aqueous medium. The intrinsically heterogeneous catalyst could be recovered after the reaction and reused without any noticeable loss in activity.

Zobrazit více v PubMed

G. S. Singh, Tetrahedron 2003, 59, 7631-7649.

F. Albericio, Curr. Opin. Chem. Biol. 2004, 8, 211-221.

B. Shen, D. M. Makley, J. N. Johnston, Nature 2010, 465, 1027-1032.

S. H. Cho, E. J. Yoo, I. Bae, S. Chang, J. Am. Chem. Soc. 2005, 127, 16046-16047.

J. S. Carey, D. Laffan, C. Thomson, M. T. Williams, Org. Biomol. Chem. 2006, 4, 2337-2347.

J. March, M. B. Smith, Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 6th ed., Wiley, Hoboken, NJ, 2007.

E. Valeur, M. Bradley, Chem. Soc. Rev. 2009, 38, 606-631.

E. Beckmann, Ber. Dtsch. Chem. Ges. 1886, 19, 988-993.

M. T. Nguyen, G. Raspoet, L. G. Vanquickenborne, J. Am. Chem. Soc. 1997, 119, 2552-2562.

R. E. Gawley, Org. React. 1988, 35, 1.

R. S. Ramón, J. Bosson, S. Díez-González, N. Marion, S. P. Nolan, J. Org. Chem. 2010, 75, 1197-1202.

M. A. Ali, T. Punniyamurthy, Adv. Synth. Catal. 2010, 352, 288-292.

H. Fujiwara, Y. Ogasawara, K. Yamaguchi, N. Mizuno, Angew. Chem. Int. Ed. 2007, 46, 5202-5205;

Angew. Chem. 2007, 119, 5294-5297.

D. Gnanamgari, R. H. Crabtree, Organometallics 2009, 28, 922-924.

N. A. Owston, A. J. Parker, J. M. J. Williams, Org. Lett. 2007, 9, 3599-3601.

N. C. Ganguly, S. Roy, P. Mondal, Tetrahedron Lett. 2012, 53, 1413-1416.

S. K. Sharma, S. D. Bishopp, C. L. Allen, R. Lawrence, M. J. Bamford, A. A. Lapkin, P. Plucinski, R. J. Watson, J. M. J. Williams, Tetrahedron Lett. 2011, 52, 4252-4255.

P. Crochet, V. Cadierno, Chem. Commun. 2015, 51, 2495-2505.

M. B. Gawande, P. S. Branco, R. S. Varma, Chem. Soc. Rev. 2013, 42, 3371-3393.

R. K. Sharma, S. Sharma, S. Dutta, R. Zboril, M. B. Gawande, Green Chem. 2015, 17, 3207-3230.

M. B. Gawande, V. D. B. Bonifacio, R. Luque, P. S. Branco, R. S. Varma, Chem. Soc. Rev. 2013, 42, 5522-5551.

S. Rostamnia, N. Nouruzi, H. Xin, R. Luque, Catal. Sci. Technol. 2015, 5, 199-205.

C. J. Li, L. Chen, Chem. Soc. Rev. 2006, 35, 68-82.

K. Yamaguchi, H. Kobayashi, Y. Wang, T. Oishi, Y. Ogasawara, N. Mizuno, Catal. Sci. Technol. 2013, 3, 318-327.

A. Martínez-Asencio, M. Yus, D. J. Ramón, Tetrahedron 2012, 68, 3948-3951.

B. K. Allam, K. N. Singh, Tetrahedron Lett. 2011, 52, 5851-5854.

R. García-Álvarez, M. Zablocka, P. Crochet, C. Duhayon, J. P. Majoral, V. Cadierno, Green Chem. 2013, 15, 2447-2456.

R. R. Gowda, D. Chakraborty, Eur. J. Org. Chem. 2011, 2226-2229.

M. E. Davis, Nature 2002, 417, 813-821.

R. Luque, A. Mariana Balu, J. Manuel Campelo, M. Dolores Gracia, E. Losada, A. Pineda, A. Angel Romero, J. C. Serrano-Ruiz, Catalysis 2012, 24, 253-280.

C. T. Kresge, M. E. Leonowicz, W. J. Roth, J. C. Vartuli, J. S. Beck, Nature 1992, 359, 710-712.

P. T. Tanev, T. J. Pinnavaia, Science 1995, 267, 865-867.

J. S. Beck, J. C. Vartuli, W. J. Roth, M. E. Leonowicz, C. T. Kresge, K. D. Schmitt, C. T. W. Chu, D. H. Olson, E. W. Sheppard, S. B. McCullen, J. B. Higgins, J. L. Schlenker, J. Am. Chem. Soc. 1992, 114, 10834-10843.

S. H. Wu, C. Y. Mou, H. P. Lin, Chem. Soc. Rev. 2013, 42, 3862-3875.

X. Fang, X. Zhao, W. Fang, C. Chen, N. Zheng, Nanoscale 2013, 5, 2205-2218.

M. B. Gawande, A. Goswami, F.-X. Felpin, T. Asefa, X. Huang, R. Silva, X. Zou, R. Zboril, R. S. Varma, Chem. Rev. 2016, 116, 3722-3811.

M. B. Gawande, A. Goswami, T. Asefa, H. Guo, A. V. Biradar, D. L. Peng, R. Zboril, R. S. Varma, Chem. Soc. Rev. 2015, 44, 7540-7590.

M. B. Gawande, A. K. Rathi, J. Tucek, K. Safarova, N. Bundaleski, N. D. Teodoro, L. Kvitek, R. S. Varma, R. Zboril, Green Chem. 2014, 16, 4137-4143.

M. B. Gawande, R. Zboril, V. Malgras, Y. Yamauchi, J. Mater. Chem. A 2015, 3, 8241-8245.

A. K. Rathi, M. B. Gawande, J. Pechousek, J. Tucek, C. Aparicio, M. Petr, O. Tomanec, R. Krikavova, Z. Travnicek, R. S. Varma, R. Zboril, Green Chem. 2016, 18, 2363-2373.

A. K. Rathi, M. B. Gawande, V. Ranc, J. Pechousek, M. Petr, K. Cepe, R. S. Varma, R. Zboril, Catal. Sci. Technol. 2016, 6, 152-160.

B. Zhao, P. Liu, H. Zhuang, Z. Jiao, T. Fang, W. Xu, B. Lu, Y. Jiang, J. Mater. Chem. A 2013, 1, 367-373.

G. V. Sagar, P. V. R. Rao, C. S. Srikanth, K. V. R. Chary, J. Phys. Chem. B 2006, 110, 13881-13888.

L. R. Azizova, T. V. Kulik, B. B. Palianytsia, A. E. Zemlyakov, V. N. Tsikalova, V. Y. Chirva, Nanoscale Res. Lett. 2014, 9, 234.

C. Henrist, K. Traina, C. Hubert, G. Toussaint, A. Rulmont, R. Cloots, J. Cryst. Growth 2003, 254, 176-187.

T. Toupance, M. Kermarec, J. F. Lambert, C. Louis, J. Phys. Chem. B 2002, 106, 2277-2286.

G. Cordoba, R. Arroyo, J. L. G. Fierro, M. Viniegra, J. Solid State Chem. 1996, 123, 93-99.

L. Chen, T. Horiuchi, T. Osaki, T. Mori, Appl. Catal. B 1999, 23, 259-269.

R. Schmidt, E. W. Hansen, M. Stoecker, D. Akporiaye, O. H. Ellestad, J. Am. Chem. Soc. 1995, 117, 4049-4056.

A. Vinu, M. Miyahara, K. Ariga, J. Phys. Chem. B 2005, 109, 6436-6441.

F. Vila, M. López Granados, M. Ojeda, J. L. G. Fierro, R. Mariscal, Catal. Today 2012, 187, 122-128.

S. Murcia-Mascarós, R. M. Navarro, L. Gómez-Sainero, U. Costantino, M. Nocchetti, J. L. G. Fierro, J. Catal. 2001, 198, 338-347.

F. Zaccheria, N. Scotti, M. Marelli, R. Psaro, N. Ravasio, Dalton Trans. 2013, 42, 1319-1328.

G. Busca, Phys. Chem. Chem. Phys. 1999, 1, 723-736.

C. J. G. Van Der Grift, A. F. H. Wielers, A. Mulder, J. W. T. Geus, Thermochim. Acta 1990, 171, 95-113.

R.-X. Zhou, T.-M. Yu, X.-Y. Jiang, F. Chen, X.-M. Zheng, Appl. Surf. Sci. 1999, 148, 263-270.

C. L. Allen, R. Lawrence, L. Emmett, J. M. J. Williams, Adv. Synth. Catal. 2011, 353, 3262-3268.

Nejnovějších 20 citací...

Zobrazit více v
Medvik | PubMed

Copper oxide-graphene oxide nanocomposite: efficient catalyst for hydrogenation of nitroaromatics in water

. 2019 Feb 21 ; 6 (1) : 6. [epub] 20190221

Najít záznam

Citační ukazatele

Pouze přihlášení uživatelé

Možnosti archivace

Nahrávání dat ...