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Supporting information
Synthesis of aryl azides from aryl halides promoted by Cu2O/tetraethylammonium prolinate
Abdol Reza Hajipour* a,b and Fatemeh Mohammadsalehb
a Department of Pharmacology, University of Wisconsin, Medical School, 1300 University Avenue, Madison, 53706-1532 WI,
USA
b Pharmaceutical Research Laboratory, Department of Chemistry, Isfahan University of Technology, Isfahan 84156, Islamic
Republic of Iran
*Corresponding author. Tel: +98-311-391-3262; Fax: +98-311-391-2351E-mail address: haji@cc.iut.ac.ir
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General procedure for synthesis of Cu2O particles:
1g of polyvinyl alcohol (crystalline powder, high molecular weight) was dissolved in 50 ml
distilled water. In another beaker, a solution of NaOH (4.0 g) in 25 ml distilled water was
prepared and this solution was added to the PVA solution under stirring; and then, the mixture
was heated at 70 ˚C for 3 h. After cooling, the solution of CuSO4.5H2O (1.25 g) in 20 ml distilled
water was added dropwise to the above PVA solution under vigorous stirring. A green gel was
produced when CuSO4 solution was added and the mixture was heated at 90 ˚C for 4 h. After
cooling the reaction mixture, ascorbic acid solution (0.89 g in 10 mL distilled water) was added
dropwise into the PVA–Cu(II) reaction mixture at room temperature under very rapid stirring.
After several seconds, the orange-red particles appeared in the reaction mixture. The resulting
mixture was then aged in air at room temperature, overnight. A reddish product obtained which
was then washed with distilled water and ethanol several times to remove impurities and dried in
air.
X-ray powder diffraction (XRD) and Scanning Electron Microscopy (SEM) analysis were used
to characterize the as-prepared Cu2O particles. The XRD pattern (Figure 1) indicates diffractions
of Cu2O particles, containing six peaks that are clearly distinguishable and all of them can be
perfectly indexed to crystalline Cu2O particles. The peak positions are in good agreement with
those for Cu2O powder reported in references (JCPDS 5-667).1
Figure 1. XRD patterns of as-prepared Cu2O particles
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The SEM images were taken with a Hitachi S-4160 Field Emission Scanning Electron
Microscopy (FESEM). The images in Figure 2 clearly manifest the Cu2O crystals with the
different diameters.
Figure 2. SEM images of synthesized Cu2O particles
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HNMR and FTIR date:
The aryl azide products are known compounds and their literature references have been provided.2-5
1-Azido-4-iodobenzene: yellow solid2, mp. 40 oC
FTIR (KBr film, cm-1): 2125, 2090.1H NMR (500 MHz, CDCl3) δ 7.67 (d, 2H), 6.82 (d, 2H).
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1-Azido-4-methoxybenzene: yellow oil3
FTIR (KBr film, cm-1): 2105.
1-Azido-3-nitrobenzene: yellow solid3, mp. 58-59 oC
FTIR (KBr film, cm-1): 2124, 2104.
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4-Azidophenol: reddish black oil4
FTIR (KBr film, cm-1): 2112, 2072.
1-Azido-4-methylbenzene: yellow oil3
FTIR (KBr film, cm-1): 2137, 2103.
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4-Azidoaniline: dark brown oil5
FTIR (KBr film, cm-1): 2111, 2075.
References
1. Joint Committee on Powder Diffraction Standards, Diffraction Data File, No. 5-667,
ICDD International Center for Diffraction Data (formerly JCPDS), Pennsylvania, USA
1991.
2. Sandler, S. R., Karo, W. Orgnic Functional Group Preparations, Vol. II. Academic
Press, London, 1971, p.266.
3. eKutonova, AK..V., Trusova, M. E., Postnikov, P. S., Filimonov, V. D., Parello, J.
Synthesis 2013, 45, 2706–2710.
4. Fotea, C., D’Silva, C. Int. J. Adhes. Adhes. 2005, 25, 442-449.
5. Grimes, K. D., Gupte, A., Aldrich, C. C. Synthesis 2010, 1, 1441–1448.
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