Fatemeh Rajabi et al.
COMMUNICATIONS
scope of the reaction is rather restricted to activated e Innovacion, Gobierno de EspaÇa through a Ramon y Cajal
contract (ref. RYC-2009-04199) and funding from MICINN
alkenes but further investigations are currently ongo-
(
project CTQ-2011-28954-C02-02) and Consejeria de Ciencia
ing in our laboratories to improve the applicability of
the nanocatalyst to less activated substrates and more
challenging systems.
e Innovacion, Junta de Andalucia (project P10-FQM-6711)
as well as the concession of a short stay fellowship under In-
centivos para Actividades de caracter cientifico y tecnico to
RL (ref. IAC-2010-2-4512) at the EPA in Cincinnati.
Experimental Section
References
Catalyst Synthesis
The preparation of supported iron oxide nanoparticles has
[1] T. Okuhara, Chem. Rev. 2002, 102, 3641–3666.
[2] a) V. Polshettiwar, R. S. Varma, Green Chem. 2010, 12,
743–754; b) V. Polshettiwar, R. S. Varma, Acc. Chem.
Res. 2008, 41, 629–639; c) J. C. Serrano-Ruiz, R. Luque,
A. Sepulveda-Escribano, Chem. Soc. Rev. 2011, 40,
5266–5281.
[3] R. Weingarten, G. A. Tompsett, W. C. Conner, G. W.
Huber, J. Catal. 2011, 279, 174–182.
[4] a) R. N. Butler, A. G. Coyne, Chem. Rev. 2010, 110,
6302–6337; b) C. J. Li, Chem. Soc. Rev. 2006, 35, 68–82.
[5] C. Gonzalez-Arellano, R. Luque, D. J. Macquarrie,
Chem. Commun. 2009, 1410–1412.
[8]
been previously reported. Full details of the characteriza-
tion of the materials have been given in the Supporting In-
formation. Briefly, SBA-15 was functionalized with amino-
propyl groups utilizing the protocol reported by Wang
[19]
À1
et al.
to achieve NH loadings of ca. 0.85–0.90 mmolg
2
and then iron oxide nanoparticles were deposited on the
[8]
materials using Fe(NO) ·9H O as precursor. The final
3
2
product was oven dried at 808C overnight prior to its use in
the catalytic reaction. Fe/SBA-15 materials had a surface
2
À1
area of 620 m g , a pore size of 4.8 nm, with nanoparticle
sizes in the 5–7 nm range, homogeneously dispersed on the
silica support (see the Supporting Information).
[6] C. Gonzalez-Arellano, J. M. Campelo, D. J. Macquarrie,
J. M. Marinas, A. A. Romero, R. Luque, Chem-
Catalytic Experiments
ACHTUNGERTNNUNGS usChem 2008, 1, 746–750.
[
7] A. Pineda, A. M. Balu, J. M. Campelo, A. A. Romero,
D. Carmona, F. Balas, J. Santamaria, R. Luque, Chem-
SusChem 2011, 4, 1561–1565.
In a typical catalytic test, styrene (5 mmol), H O (5 mmol,
2
2
50% v/v aqueous solution) and 0.5 mol% of Fe/SBA-15 ma-
terials in 2 mL water were refluxed (1008C) for 4–6 h. Upon
completion, as indicated by TLC, the final mixture was fil-
tered off to recover the catalyst, which was washed with
ethyl acetate and subsequently dried at 808C prior to its
reuse in the reaction. The combined filtrate and ethyl ace-
tate washings were then washed with water and the organic
layer separated and dried over magnesium sulfate. The
product from the organic solution was obtained upon sol-
[
8] F. Rajabi, S. Naresian, A. Primo, R. Luque, Adv. Synth.
Catal. 2011, 353, 2060–2066.
[
9] R. Luque, J. H. Clark, K. Yoshida, P. L. Gai, Chem.
Commun. 2009, 5305–5307.
[
[
10] C. Vargas, A. M. Balu, J. M. Campelo, C. Gonzalez-
Arellano, R. Luque, A. A. Romero, Curr. Org. Synth.
2
010, 7, 568–586.
11] A. Pineda, A. M. Balu, J. M. Campelo, R. Luque, A. A.
Romero, J. C. Serrano-Ruiz, Catal. Today 2011, in
press.
1
vent removal. The conversion was determined by H NMR
(
400 MHz) spectroscopic analysis and compounds were char-
acterised by GC and GC/MS. In most cases, products could
be isolated in their pure forms by simple filtration and evap-
oration of the solvent. Further purification required column
chromatography in some cases. The isolated products all
known compounds which have been previously identified
[
12] A. M. Balu, J. M. Campelo, R. Luque, A. A. Romero,
Org. Biomol. Chem. 2010, 8, 2845–2849.
[
13] a) H. J. Shipley, K. E. Engates, A. M. Guettner, J.
Nanopart. Res. 2011, 13, 2387–2397; b) M. Tong, S. H.
Yuan, H. Y. Long, M. M. Zheng, L. L. Wang, J. Chen, J.
Contam. Hydrol. 2011, 122, 16–25.
[20,21]
and characterized in several literature reports.
[
14] V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouh-
rara, J. M. Basset, Chem. Rev. 2011, 111, 3036–3075.
15] N. Miguel-Sancho, O. Bomati-Miguel, G. Clom, J. P.
Salvador, M. P. Marco, J, Santamaria, Chem. Mater.
Recyclability Experiments
[
Upon completion of the first reaction to afford a quantitative
yield of the corresponding aldehyde (>95% yield), the cata-
lyst was recovered by filtration, washed with acetone and
ethanol and oven dried at 808C overnight. A new reaction
was then performed with fresh solvent and reactants under
identical conditions.
2
011, 23, 2795–2802.
[
16] T. Hoare, B. P. Timko, J. Santamaria, G. F. Goya, S.
Irusta, S. Lau, C. F. Stefanescu, D. B. Lin, R. Langer,
D. S. Kohane, NanoLett. 2011, 11, 1395–1400.
17] T. Zeng, W. W. Chen, C. M. Cirtiu, A. Moores, G. Song,
C. J. Li, Green Chem. 2010, 12, 570–573.
18] a) M. Sasidharan, A. Bhaumik, J. Mol. Catal. A 2010,
[
[
3
28, 60–67; b) M. Guidotti, C. Pirovano, N. Ravasio, B.
Acknowledgements
Lazaro, J. M. Fraile, J. A. Mayoral, B. Coq, A. Galar-
neau, Green Chem. 2009, 11, 1421–1427; c) S. K. Maiti,
K. M. A. Malik, S. Gupta, S. Chakraborty, A. K. Gang-
uli, A. K. Mukherjee, R. Bhattacharyya, Inorg. Chem.
2006, 45, 9843–9857; d) S. Nlate, L. Plault, D. Astruc,
FR is grateful to Payame Noor University and Iran National
Science Foundation (INSF) for support of this work. RL
gratefully acknowledges support from Ministerio de Ciencia
1710
ꢃ 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2012, 354, 1707 – 1711