Abstract
A facile method was developed for the synthesis of β-azido alcohols and β-nitro alcohols in the presence of a novel nano-Fe3O4-copoly[(styrene/acrylic acid)/grafted ethylene oxide (nano-Fe3O4-PS-Co-[PAA-g-PEG]) as a phase-transfer catalyst in water. The catalyst was characterized with IR, SEM, and TGA. This procedure offers several advantages, including excellent regioselectivity, high yields, short reaction times, a recyclable catalyst, easy separation of the catalyst through an external magnet, and easy workup .
Similar content being viewed by others
References
Y. Zhu, L.P. Stubbs, F. Ho, R. Liu, C.P. Ship, J.A. Maguire, N.S. Hosmane, ChemCatChem 2, 365–374 (2010)
S. Laurent, D. Forge, M. Port, A. Roch, C. Robic, L.V. Elst, R.N. Muller, Chem. Rev. 108, 2064–2110 (2008)
V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J.-M. Basset, Chem. Rev. 111, 3036–3075 (2011)
S. Igder, A.R. Kiasat, M.R. Shushizadeh, Res. Chem. Intermed. doi:10.1007/s11164-014-1808-1
M.B. Gawande, P.S. Branco, R.S. Varma, Chem. Soc. Rev. 42, 3371 (2013)
H.E.S. Ali, Catal. Commun. 8, 855–860 (2007)
H. Mahdavi, B. Tamami, React. Funct. Polym. 64, 179–185 (2005)
Y.R. Jorapur, G. Rajagopal, P.J. Saikia, R.R. Pal, Tetrahedron Lett. 49, 1495–1497 (2008)
S.W. Chen, S.S. Thakur, W. Li, C.K. Shin, R.B. Kawthekar, G.J. Kim, J. Mol. Catal. 259, 116–120 (2006)
F. Fringuelli, O. Piermatti, F. Pizzo, L. Vaccaro, J. Org. Chem. 64, 6094–6096 (1999)
G. Sabitha, R.S. Babu, M. Rajkumar, J.S. Yadav, Org. Lett. 4, 343–345 (2002)
B. Tamami, H. Mahdavi, Tetrahedron Lett. 42, 8721–8724 (2001)
J.H.L. Spelberg, J.E.T.H. Vlieg, L. Tang, D.B. Janssen, R.M. Kellogg, Org. Lett. 3, 41–43 (2001)
G. Sabitha, R.S. Babu, M.S.K. Reddy, J.S. Yadav, Synthesis 15, 2254–2258 (2002)
F. Kazemi, A.R. Kiasat, S. Ebrahimi, Synth. Commun. 33, 999–1004 (2003)
N. Iranpoor, H. Firouzabadi, M. Shekarize, Org. Biomol. Chem. 1, 724–727 (2003)
S.W. Chen, S.S. Thakur, W. Li, C.K. Shin, R.B. Kawthekar, G.J.J. Kim, Mol. Catal. A: Chem. 259, 116 (2006)
B. Yadollahi, H. Danafar, Catal. Lett. 113, 120–123 (2007)
A.R. Kiasat, R. Badri, B. Zargar, S. Sayyahi, J. Org. Chem. 73, 8382–8385 (2008)
B. Sreedhar, P. Radhika, B. Neelima, N. Hebalkar, J. Mol. Catal. A: Chem. 272, 159–163 (2007)
A.R. Kiasat, M. Zayadi, Catal. Commun. 9, 2063–2067 (2008)
A.R. Kiasat, S. Sayyahi, Catal. Commun. 11, 484–486 (2010)
A.R. Kiasat, A. Mouradzadegun, S.J. Saghanezhad, Res. Chem. Intermed. 41, 319–326 (2015)
K. Can, M. Ozmen, M. Ersoz, Colloids Surf. B 71, 154–159 (2009)
A. Kamal, M. Arifuddin, M.V. Rao, Tetrahedron Asymmetry 10, 4261 (1999)
B. Das, S.V. Reddy, M. Krishnaiah, Y.K. Rao, J. Mol. Catal. A: Chem. 270, 89 (2007)
A.R. Kiasat, R. Mirzajani, H. Shalbaf, T. Tabatabaei, M. Fallah-Mehrjardi, J. Chin. Chem. Soc. 56, 594 (2009)
A.R. Kiasat, M. Fallah-Mehrjardi, J. Iran. Chem. Soc. 6, 542 (2009)
H. El Ghandoor, H.M. Zidan, M.M.H. Khalil, M.I.M. Ismail, Int. J. Electrochem. Sci. 7, 5734–5745 (2012)
Acknowledgments
We are grateful to the Research Council of Shahid Chamran University for financial support.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kiasat, A.R., Daei, M. & Saghanezhad, S.J. Synthesis and characterization of a novel nano-Fe3O4-copoly[(styrene/acrylic acid)/grafted ethylene oxide and its application as a magnetic and recyclable phase-transfer catalyst in the preparation of β-azido alcohols and β-nitro alcohols. Res Chem Intermed 42, 581–594 (2016). https://doi.org/10.1007/s11164-015-2043-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-015-2043-0