RSC Advances
DOI: 10.1039/C4RA08726G
conditions. The catalytic beads were separated after 0.5h by
external magnet and continue the reaction in absence of catalyst
for 2h. The reaction was monitored on GC with respective time
quantity. The recovered catalyst showed excellent stability and
recyclability up to fifth cycle.
and the obtained results are shown in Fig. 8a. The graph plotted 60 Acknowledgements
5
0
5
0
5
0
5
0
GC yield (%) versus time (h) represents the comparison between
yield obtained in presence of catalyst (Standard Curve) and yield
obtained in absence of catalyst after 0.5h. Similarly, the test has
been also performed for scheme 3 in DMSO. The reaction of
The authors are very thankful to the UGCꢀUPE Green
Technology centre, New Delhi, India for awarding the
fellowship. The authors also thankful to Prof. C. V. Tomy,
Department of Physics, IIT Bombay and SAIF Department IIT
iodobenzene and morpholine has been carried out under the 65 Bombay.
optimised conditions. After 4h the catalyst was separated and
1
1
2
2
3
3
4
continues the reaction for 12h. The reaction was monitored on
GC and the obtained results are plotted with the results of
reaction with catalyst (Fig. 8b).
Notes and references
a
Department of Chemistry, Institute of Chemical Technology, Matunga,
Mumbai – 400019, India. Fax: +91 22 33611020; Tel.: +91 22
3611111/2222; E-mail: jm.nagarkar@ictmumbai.edu.in
3
70 † Electronic Supplementary Information (ESI) available: [Experimental
procedures, Catalyst charactrization, Mass and H NMR Spectra of
synthesized compound]. See DOI: 10.1039/b000000x/
1
1
.
A. K. Verma, R. R. Jha, R. Chaudhary, R. K. Tiwari and A. K.
Danodia, Adv. Synth. Catal., 2013, 355, 421ꢀ438; R. Shelkar, S.
Sarode and J. Nagarkar, Tetrahedron Lett., 2013, 54, 6986ꢀ6990; C.
Liu, H. Zhang, W. Shi and A. Lei, Chem. Rev., 2011, 111,1780ꢀ1824.
7
8
8
9
9
5
0
5
0
5
2
. J. Mondal, A. Modak and A. Bhaumik, J. Mol. Catal. A: Chem., 2011,
50, 40ꢀ48; R. J. Kalbasi, N. Mosaddegh and A. Abbaspourrad,
Tetrahedron lett., 2012, 53, 3763ꢀ3766.
3
3. H. Li, M. Yang and Q. Pu, Microporous Mesoporous Mater., 2012,
148, 166ꢀ173; B. W. Glasspoole, J. D. Webb and C. M. Crudden, J.
Catal., 2009, 265, 148ꢀ154.
Fig. 8 The plot of GC yield (%) versus time (h) for (a) Scheme 1
and (b) Scheme 3.
4
.
S. Gao, N. Zhao, M. Shu and S. Che, Appl. Catal. A: Gen., 2010, 388,
96ꢀ201; A. Gomann, J. A. Deverell, K. F. Munting, R. C. Jones, T.
Rodemann, A. J. Canty, J. A. Smith and R. M. Guijit, Tetrahedron,
009, 65, 1450ꢀ1454.
The graphs show that after catalyst separation the product yield
was not increased. Therefore from the above test which was
carried out for scheme 1 and scheme 3 in water and DMSO
respectively, it was clear that the leaching of the catalyst was
insignificant and this was also confirmed by ICPꢀAES analysis.
1
2
5. A. S. Guram, R. A. Rennels and S. L. Buchwald, Angew. Chem. Int.
Ed., 1995, 34, 1348ꢀ1350; J. Louie and J. F. Hartwig, Tetrahedron
Lett., 1995, 36, 3609ꢀ3612.
6. X. F. Wu, P. Anbarasan, H. Neumann and M. Beller, Angew. Chem.
Int. Ed., 2010, 9047; P. W. N. M. Van Leeuwen Kluwer Academic
Publisher, London, 2004, 271ꢀ298.
7
.
J. Lim and E. E. Simanek, Adv. Drug Deliv. Rev., 2012, 64, 826ꢀ835;
T. H. M. Jonckers, B. U. W. Maes, G. L. F. Lemiere and R.
Dommisse, Tetrahdron, 2001, 57, 7027ꢀ7034.
8
9
. Z. Jin, L. L. Qiu, Y. Q. Li, H. B. Song and J. X. Fang,
Organometallics, 2010, 29, 6578ꢀ6586.
. W. A. Herrmann, C. Brossmer, K. Ofele, C. P. Reisinger, T.
Priermeier, M. Beller and H. Fisher, Angew. Chem. Int. Ed. Engl.,
1995, 34, 1844; X. Gai, R. Grigg, M. L. Ramzan, V. Sridharan, S.
Collard and J. E. Muir, Chem. Commun., 2000, 2053; S. Gibson, D.
F. Foster, G. R. Eastam, R. P. Tooze and D. J. ColeꢀHamilton, Chem.
Commun., 2001, 779.
1
1
1
1
1
00
05
10
Fig. 9 Possible mechanism for Scheme 1, 2 and 3.
10. D. Bourissou, O. Guerret, F. P. Gabbai and G. Bertrand, Chem. Rev.,
2000,100, 39; N. Marion and S. P. Nolan, Acc. Chem. Res., 2008, 41,
1
440.
Conclusions
1
1. D. F. Wass, M. F. Haddow, T. W. Hey, A. Guy Orpen, C. A. Russell,
R. L. Wingad and M. Green, Chem. Commun., 2007, 2704; W. A.
Herrmann, K. Ofele, S. K. Schneider, E. Herdtweck and S. D.
Hoffmann, Angew. Chem. Int. Ed., 2006, 45, 3859.
4
5
5
5
0
5
In conclusion, we reported a simple preparation of beads of
magnetic nano PdꢀFe O @Alg catalyst and its successful
3
4
applications for Suzuki, Heck coupling reactions in aqueous
medium and Buchwald Hartwig amination reactions in DMSO
under ligand free conditions. The reported catalytic system is
very simple, efficient, economical and environmentally
favourable with outstanding product yields. This heterogeneous
catalyst works in the same way for the structurally and
electronically varied aryl halides, boronic acids, olefins and
amines giving moderate to excellent yield of the corresponding
products. Moreover, the catalyst was easy to handle and separate
by simple filtration or by magnetic separation without any loss in
1
2. J. Tong, Z. Li and C. Xia, J. Mol. Catal. A: Chem., 2005, 231, 197; T.
Vincent and E. Guibal, Langmuir, 2003, 19, 8475.
13. V. L. Budarin, J. H. Clark, R. Luque, D. J. Macquarrie and R. J.
White, Green Chem., 2008, 10, 382.
15 14. M. R. Mucalo, C. R. Bullen and M. ManleyꢀHarris, J. Mater. Sci.,
002, 37, 493.
2
1
5. S. Ahmadi, M. Outokesh, M. Hosseinpour and T. Mousavand,
Particuology, 2011, 9,480ꢀ485; Z. Wang, G. Kale, Q. Yuag and M.
Ghadiri, RSC Adv., 2012, 2, 9993ꢀ9997; A. Primo, T. Marino, A.
Corma, R. Molinari and H. Garcia, J. Am. Chem. Soc., 2011, 133,
20
6
930ꢀ6933.
1
6. L. H. Fan, Y. L. Luo, Y. S. Chen, C. H. Zhang and Q. B. Wei, J.
Nanopart Res., 2011, 11, 449ꢀ458; D. Shao, A. Xia, J. Hu, C. Wang
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