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COMMUNICATION
Journal Name
Wiley: VCH, 2008.
DOI: 10.1039/C6RA09659J
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00
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4
G. Brieger and T. J. Nestrick, Chem. Rev. 1974, 74, 567.
(
a) Complete run
(a) A. Hu, G. T. Yee and W. Lin, J. Am. Chem. Soc., 2005, 127
,
(b) Filtrate recovered after 30 min
80
60
40
20
0
1
2486; (b) R. Abu-Reziq, H. Alper, D. Wang and M. L. Post, J.
Am. Chem. Soc., 2006, 128, 5279; (c) C. O. Dalaigh, S. A. Corr,
Y. Gunko and S. J. Connon, Angew. Chem., Int. Ed., 2007, 46
,
4
329; (d) T. Hara, T. Kaneta, K. Mori, T. Mitsudome, T.
Mizugaki, K. Ebitanic and K. Kaneda, Green Chem., 2007,
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,
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2
246; (e) A. H. Latham and M. E. Williams, Acc. Chem. Res.,
008, 41, 411.
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(a) B. Baruwati, D. Guin and S. V. Manorama, Org. Lett.,
007, , 5377–5380; (b) B. Baruwati, V. Polshettiwar and R.
S. Varma, Tetrahedron Lett., 2009, 50, 1215; (c) D. Guin, B.
Baruwati and S. Manorama, Org. Lett., 2007, , 1419; (d) W.-
2
9
9
0
20
40
60
80
100
120
140
160
J. Liu, K. Tian and H. Jiang, Green Chem., 2015, 17, 821; (e) R.
B. N. Baig, and R. S. Varma, ACS Sustainable Chem. Eng.,
Reaction time (Minutes)
2
013, 1, 805; (f) M. B. Gawande, A. K. Rathi, P. S. Branco, I. D.
Figure 3 Results of leaching study by hot filtration test
performed with: (a) complete run (black line) and (b) filtrate
Nogueira, A. Velhinho, J. J. Shrikhande, U. U. Indulkar, R. V.
Jayaram, C. A. A. Ghumman, N. Bundaleski and O. M. N. D.
Teodoro, Chem. Eur. J., 2012, 18, 12628; (g) A. M. Kulkarni,
U. V. Desai, K. S. Pandit, M. A. Kulkarnia and P. P.
removed after 30 min. (red line) for the hydrogenation of
nitrostyrene.
-
Wadgaonkar, RSC Adv., 2014,
Moghaddam, G. Tavakoli and H. R. Rezvani, Catal. Commun.,
015, 60, 82; (i) F. M. Moghaddam, B. K. Foroushani and H.
R. Rezvani, RSC Adv., 2015, , 18092; (j) F. M. Moghaddam,
G. Tavakoli and A. Aliabadi, RSC Adv., 2015, , 59142; (k) V.
4, 36702; (h) F. M.
2
Conclusions
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5
In conclusion, we have demonstrated a simple, efficient and
green protocol for the highly regio- and chemoselective
transfer hydrogenation of olefins and alkynes using magnetic
nano-NiFe O as reusable catalyst. The protocol is very clean
Polshettiwar, B. Baruwati and R. S. Varma, Green Chem.,
2009, 11, 127.
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(a) S. Banerjee and S. Santra, Tetrahedron Lett., 2009, 50
,
2
037; (b) S. Banerjee and G. Sereda, Tetrahedron Lett., 2009,
, 6959; (c) S. Banerjee, J. Das, R. Alverez and S. Santra,
302; (d) S. Banerjee, V.
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0
and mild. This is the first transfer hydrogenation using only
bare nano-NiFe O in absence of precious and costly metals
New J. Chem., 2010, 34
,
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4
Balasanthiran, R. Koodali and G. Sereda, Org. Biomol. Chem.
2010, , 4316; (e) S. Banerjee, A. Horn, H. Khatri and G.
such as ruthenium/palladium. In addition, we have also
reported here dehydrogenation of alcohol using bare nano-
NiFe O catalyst. This present method does not require any
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Sereda, Tetrahedron Lett., 2011, 52, 1878; (f) S. Banerjee and
A. Saha, New J. Chem. 2013, 37, 4170; (g) S. Payra, A. Saha,
G. Sereda and S. Banerjee, Tetrahedron Lett., 2014, 55, 5515;
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base or ligand. Moreover, magnetic nature of nano-NiFe O
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4
(
h) A. Saha, S. Payra and S. Banerjee, Green Chem. 2015, 17,
enables easy separation of catalyst after reaction by using
external magnet and made the protocol environmentally
benign in nature.
2
859; (i) S. Banerjee, New J. Chem., 2015, 39, 5350; (j) A.
Saha, S. Payra and S. Banerjee, RSC Adv., 2015,
A. Saha, S. Payra, S. K. Verma, M. Mandal, S. Thareja, and S.
Banerjee, RSC Adv., 2015,
S. Banerjee, RSC Adv , 2016,
S. Guchhait and S. Banerjee, RSC Adv., 2016,
General experimental procedure for NiFe O NPs catalyzed
5
, 101664; (k)
5
, 100978; (l) S. Payra, A. Saha and
, 12402; (m) S. Payra, A. Saha,
, 33462.
.
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Notes and references
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We are pleased to acknowledge Department of Science and
Technology, New Delhi, Govt. of India (NO.SB/FT/CS-023/2012)
for the financial support. Special thanks to Prof. B. C. Ranu and
his group for their help in NMR studies.
transfer hydrogenation of alkenes: Representative
procedure for the hydrogenation of methoxy-4-((E)-2-
nitroethyl)benzene.
A
mixture of methoxy-4-((E)-2-
nitroethyl)benzene (1 mmol), isopropyl alcohol (2 ml) and
o
NiFe O (10 mg) is heated at 80 C under open atmosphere
2 4
1
(a) G. Brieger and T. Nestrick, J. Chem. Rev. 1974, 74, 567; (b)
R. A. W. Johnstone, A. H. Wilby and I. D. Entwistle Chem. Rev.
for 3 h (TLC-monitored). Then, the reaction mixture was
cooled to room temperature and magnetic NPs were
separated by using external magnet. The remaining was
extracted with ethyl acetate, washed with water followed by
1
1
985, 85, 129; (c) G. Zassinovish and G. Mestroni, Chem. Rev.
992, 92, 1051; (d) R. Noyori and S. Hashiguchi, Acc. Chem.
Res. 1997, 30, 97; (e) K. Everaere, A. Mortreux and J.-F.
Carpentier, Adv. Synth. Catal. 2003, 345, 67; (f) S. Gladiali
and E. Alberico, Chem. Soc. Rev. 2006, 35, 226; (g) T. Ikariya
and A. J. Blacker, Acc. Chem. Res. 2007, 40, 1300; (h) X. Wu
and J. Xiao, Chem. Commun. 2007, 2449; (i) B. Zhao, Z. Han
and K. Ding, Angew. Chem., Int. Ed. 2013, 52, 4744; (j) R.
Malacea, R. Poli and E. Manoury, Coord. Chem. Rev. 2010,
brine solution and dried over anhydrous Na SO . The crude
2 4
product was obtained by evaporation of solvent in vacuum
which was purified by column chromatography over silica gel
(60–120 mesh) using mixture of petroleum ether and ethyl
acetate (95:5) as an eluting solvent to afford the pure
methoxy-4-(2-nitroethyl)benzene (Table 2, 2; 85%, 150.37
mg) as pale yellow oil. The formation of the product was
1
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2
54, 729; (k) S. E. Clapham, A. Hadzovic and R. H. Morris,
confirmed by spectroscopic studies ( H NMR) studies. H
Coord. Chem. Rev. 2004, 248, 2201.
NMR (500 MHz, CDCl ): δ 8.01 (d, J = 8.5 Hz, 2H), 6.92 (d, J =
3
9.0 Hz, 2H), 4.44 (d, J = 4.5 Hz, 2H), 3.94 (d, J = 4.5 Hz, 2H),
2
(a) J. E. J. Bäckvall, Organomet. Chem. 2002, 652, 105; (b) M.
D. Le Page and R. B. James, Chem. Commun. 2000, 17, 1647;
(c) G. Szollosi and M. Bartok, Catal. Lett. 1999, 59, 179; (d) P.
3.86 (s, 3H).
The same protocol was followed for all the reaction listed in
Table 2.
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