NaBH4/Ac2O/DOWEX(R)50WX4: A convenient system for fast preparation of gem-diacetates from aldehydes

Article abstract of DOI:10.1002/jccs.201400049

Reductive-acylalation of aldehydes has been carried out by NaBH ₄/Ac₂O/DOWEX(R)50WX4 system. A variety of aldehydes (1 mmol) have been reacted with Ac₂O (0.5 mL) and NaBH₄ (1 mmol) in the presence of DOWEX(R)50WX4 (0.5 g) for the preparation of their corresponding acylals within 1 min at room temperature with excellent yields of the products (90-95%). Ketones do not react with this system.

Full text of DOI:10.1002/jccs.201400049

JOURNAL OF THE CHINESE
CHEMICAL SOCIETY
Article
NaBH4/Ac2O/DOWEX(R)50WX4: A Convenient System for Fast Preparation of
gem-Diacetates from Aldehydes
Parisa Azizi Asl and Davood Setamdideh*
Department of Chemistry, College of Sciences, Mahabad Branch, Islamic Azad University, Mahabad, Iran
(Received: Jan. 30, 2014; Accepted: Feb. 27, 2014; Published Online: Apr. 23, 2014; DOI: 10.1002/jccs.201400049)
Reductive-acylalation of aldehydes has been carried out by NaBH4/Ac2O/DOWEX(R)50WX4 system. A
variety of aldehydes (1 mmol) have been reacted with Ac2O (0.5 mL) and NaBH4 (1 mmol) in the presence
of DOWEX(R)50WX4 (0.5 g) for the preparation of their corresponding acylals within 1 min at room
temperature with excellent yields of the products (90-95%). Ketones do not react with this system.
Keywords: NaBH4; DOWEX(R)50WX4; Acylal; gem-Diacetate; Aldehyde.
INTRODUCTION
The protection of carbonyl functional group of alde-
harsh reaction conditions, long reaction times, use of
strong acids, strictly reaction conditions, moisture sensitiv-
ity, high toxicity (several of these catalysts are unsafe to
handle) as well as high cost of the reagents and unavailable
catalyst. Thus, the search for new reagents and methods is
still of practical importance. Our literature review did not
show any application of the reducing agents as a promoter
in the acylalation of aldehydes. Therefore, this subject and
in continuation of our ongoing research program on the de-
velopment of new methods for the functional group trans-
formations,51-61 encourage us to investigate reductive-
acylalation of aldehydes. Herein, we describe the fast and
efficient method for the reductive-acylalation of a variety
of aldehydes to their corresponding gem-diacetates with
NaBH4/Ac2O in the presence of DOWEX(R)50WX4 as
acidic surface catalyst.
hydes is important in organic synthesis. This goal can be
achieved by the preparation of gem-diacetates (Acylals)
from the corresponding aldehydes.1 Acylals have several
synthetic applications, because acylals are stable under
critically controlled acidic, neutral and basic conditions.
They were utilized as cross linking reagents2 in cellulose
and cotton industry. Also, acylals have been used in the
some famous organic reactions, such as starting materials
for Diels-Alder reactions,3 Grignard,4a Barbier,4b Prins re-
actions,5 Knoevenagel6a and benzoin condensation.6b
Acylals are also used in the synthesis of chrysanthemic
acid,7a and sphingofungins E and F.7b Several reagents or
catalysts such as Amberlyst,8 Envirocatsw,9 Montmorillo-
nite,10 Zeolites,11 Nafion-H,12 FeSO4,13 FeCl3,14 AlCl3,15
TMSCl-NaI,16 Sc(OTf)3,17 I2,18 NBS,19 PCl3,20 H2SO4,21
Cu(OTf)2,22 LiBF4,23 H2NSO3H,24 InCl3,25 (NH4)2Ce(NO3)6,26
LiOTf,27 Zn(BF4)2,28 AlPW12O40,29 ZrCl4,30 Bi(NO3)3.
5H2O,31 Bi(CF3SO3).4H2O,32 Zirconium Sulfohenyl Phos-
phonat,33 GaCl3,34 GaI3,35 Sulphated Zirconia,36 Poly(N,N¢-
dibromo-N-ethyl-benzene-1,3-disulfonamide) [PBBS] &
N,N,N¢,N¢-tetrabromobenzene-1,3-disulfonamide
[TBBDA],37 Saccharin Sulfonic Acid,38 Zirconium Hydro-
gen Sulfate,39 Fe2(SO4)3·xH2O,40 Erbium triflate,41 Alum-
[KAl(SO4)2.12H2O],42 Sulfated Zirconia,43 KHCO3,44
H2SO4-silica,45 Indium Tribromide,46 HClO4-SiO2,47 solid
lithium perchlorate,48 Zinc(II) perchlorate,49 [Hmim] HSO4
[Brönsted acidic ionic liquid],50 have been employed for
the preparation of acylals. These methods have some ad-
vantages such as high yields of the corresponding diace-
tates. However, they have the major disadvantages such as
RESULTS AND DISCUSSION
Recently, we have reported that the DOWEX(R)50WX4
can be used for the regioselective synthesis of Oximes by
NH2OH.HCl/DOWEX(R)50WX4 system,58 reduction of a
variety of carbonyl compounds such as aldehydes, ketones,
a-diketones, acyloins and a,b-unsaturated carbonyl com-
pounds to their corresponding alcohols by NaBH4/
DOWEX(R)50WX4 system,59 synthesis of cyanohydrins
by NaCN/DOWEX(R)50WX460 and reductive-amination
of a variety of aldehydes and anilines by NaBH4/
DOWEX(R)50WX4.61 In this context, we now wish to re-
port an efficient, facile acylalation of aldehydes by NaBH4/
Ac2O/DOWEX(R)50WX4 at room temperature.
The model reaction has been selected by reductive-
acylalation of benzaldehyde. This reaction was carried out
* Corresponding author. E-mail: davood.setamdideh@gmail.com; d.setamdideh@iau-mahabad.ac.ir
Supporting information for this article is available on the www under http://dx.doi.org/10.1002/jccs.201400049
940
© 2014 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
J. Chin. Chem. Soc. 2014, 61, 940-944

JOURNAL OF THE CHINESE
CHEMICAL SOCIETY
Fast Preparation of gem-Diacetates from Aldehydes
Table 1. Optimization of the Reductive-Acylalation of Benzaldehyde (1 mmol) to 1,1-diacetoxy-1-phenylmethane
with NaBH4 and DOWEX(R)50WX4 at RT
Entry NaBH4 (mmol) DOWEX(R)50WX4 (g)
Solvent (mL)
Time (min)
Conversiona (%)
1
0
0
0.5
0.5
0.5
0.5
0.5
0.5
0.25
EtOAc (0.5)
Ac2O (0.5)
30
30
30
1
0
0
2
3
1
EtOAc (0.5)
0
4
1
Ac2O (0.5)
100
100 ?
100 ?
100 ?
5b
6b
7b
1
EtOAc/Ac2O (0.25:0.25)
Ac2O (0.5)
30
30
30
0.5
1
Ac2O (0.5)
a Conversions refer to 1,1-diacetoxy-1-phenylmethane and were monitored by TLC (eluent; n-hexane/EtOAc: 9/1).
b A mixture of the products obtained (1,1-diacetoxy-1-phenylmethane and benzyl alcohol, the products were not
separated).
Scheme II
in different conditions (different amounts of NaBH4, Ac2O,
DOWEX(R)50WX4 and different solvents) for the selec-
tion of appropriate conditions at room temperature as
shown in Table 1. Among the tested different solvents, the
reaction was most facile and proceeded to give the highest
yield in Ac2O. The optimization reaction conditions showed
that using 1 molar equivalents of NaBH4 and 0.5 g of
DOWEX(R)50WX4 in 0.5 mL Ac2O were the best condi-
tions to complete the reductive-acylalation of benzaldehye
(1 mmol) to gem-benzyldiacetate (Table 1, Entry 4). Our
observation revealed that reductive-acylalation is com-
pleted within 1 min with 91% yields of product as shown in
Scheme I.
namaldehyde with 1 molar equivalents of NaBH4 and 0.5
mL Ac2O in the presence of 0.5 g of DOWEX(R)50WX4
was carried out exclusively in 1,2-reduction manner within
1 min at room temperature as shown in Scheme III. In this
reaction the corresponding cinnamyl acylal was obtained in
93% yield (Table 2, entry 14).
Scheme I
Scheme III
The efficiency of this protocol was further examined
by using various structurally different aldehydes. In this
approach, the corresponding acylals were obtained in ex-
cellent yields (90-95%) within 1 min as shown in Table 2.
Since the insolubility of DOWEX(R)50WX4 in Ac2O,
the reaction takes places under heterogeneous conditions.
The mechanism for the influence of DOWEX(R)50WX4 is
not clear, but as shown in Scheme II, we think that SO3H
groups on DOWEX(R)50WX4 (as cation exchange resin,
strong acid) protonate the carbonyl group of aldehydes
(Scheme II, step I) which make it more susceptible for
Ac2O attack (Scheme II, step II). Also, this reaction can be
promoted by the hydride attack from NaBH4 (Scheme II,
step III). We observed that hydrogen gas is slowly liberated
in situ (Scheme II, step IV).
Our next attempt was the preparation of gem-diace-
tates from ketones by the NaBH4/DOWEX(R)50WX4/
Ac2O system. Our experiments showed that ketones do not
react with this system.
We have also checked the reusability of the catalyst
using the recovered DOWEX(R)50WX4 from the reduc-
tive-acylalation reaction. It was observed that recovered
catalyst could not be satisfactorily used for the second run
without regeneration and it leads to poor yields and longer
reaction times. Whereas, after regeneration of
DOWEX(R)50WX4 (It was stirred in HCl 10-5% for 30-60
min, then washed with distillated water), the reductive-
On the other hand, the reductive-acylalation of cin-
J. Chin. Chem. Soc. 2014, 61, 940-944
© 2014 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.jccs.wiley-vch.de
941

Article
Asl and Setamdideh
Table 2. Reductive-acylalation of Aldehydes (1 mmol) with Ac2O (0.5 mL) by NaBH4 (1 mmol) in the presence of DOWEX(R)50WX4
(0.5 g) at RT
Time Yields
1H-NMR
(%)a d CH (ppm) n C=O (cm-1) (ºC)b
FT-IR
m.p.
Entry
Aldehydes
Products
(min)
1
benzaldehyde
1,1-diacetoxy-1-phenyl methane
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
91
95
93
95
92
93
92
95
95
90
92
91
94
93
92
90
7.69
7.62
7.54
7.62
7.78
7.67
7.73
7.74
7.61
7.47
8.03
7.62
7.66
7.38
7.70
6.81
1761
1764
1760
1760
1761
1763
1759
1760
1738
1757
1761
1752
1759
1762
1763
1755
44-45
94-95
52-53
83-84
64-65
99-101
124-125
66-67
65-66
oil
2
4-bromobenzaldehyde
2-chloronzaldehyde
4-chlorobenzaldehyde
3-chlorobenzaldehyde
1,1-diacetoxy-1-(4-bromophenyl) methane
1,1-diacetoxy-1-(2-chlorophenyl) methane
1,1-diacetoxy-1-(4-chlorophenyl) methane
1,1-diacetoxy-1-(3-chlorophenyl) methane
3
4
5
6
2,4-dichlorobenzaldehyde 1,1-diacetoxy-1-(2,4-dichlorophenyl) methane
7
4-nitrobenzaldehyde
3-nitrobenzaldehyde
1,1-diacetoxy-1-(4-nitrophenyl) methane
1,1-diacetoxy-1-(3-nitrophenyl) methane
1,1-diacetoxy-1-(4-methoxyphenyl) methane
1,1-diacetoxy-1-(3-methoxyphenyl) methane
1,1-diacetoxy-1-(2-methoxyphenyl) methane
8
9
4-methoxybenzaldehyde
3-methoxybenzaldehyde
2-methoxybenzaldehyde
10
11
12
13
14
15
16
69-70
64-65
80-81
83-85
52-53
oil
3,4-dimethoxybenzaldehyde 1,1-diacetoxy-1-(3,4-dimethoxyphenyl) methane
4-methylbenzaldehyde
cinnamaldehyde
furforal
1,1-diacetoxy-1-(4-methylphenyl) methane
1,1-diacetoxy-1-(cinammyl) methane
1,1-diacetoxy-1-furyl methane
1,1-diacetoxybutane
butanal
a Yields refer to isolated pure products ( 3%). b The melting points were compared with the literature.46-50
acylalation reactions have been carried out like the first run
in the presence of the regenerated DOWEX(R)50WX4.
The products were characterized by the 1H-chemical
shift of the CH group which appears around 6.8-8 ppm as a
singlet (1H) and gem-diacetate group which appears around
2.1 ppm as a singlet (6H). Also the C=O stretching fre-
quency in FT-IR spectrum appears around 1738-1763 cm-1
as shown in Table 2.
(eluent; n-hexan/EtOAc: 9/1). The reaction was filtered after
completion within 1 min. After completion of the reaction, the
catalyst was filtered and washed with ethyl acetate (15 mL). The
combined organic layers were washed with saturated NaHCO3 so-
lution (3 × 10 mL) and water (10 mL) and then dried over anhy-
drous Na2SO4. The solvent were removed on a rotary evaporator
under reduced pressure to give pure product. 1,1-diacetoxy-1-
phenylmethane has been obtained (0.l89 g, 91% yield, Table 2,
entry 1) which was characterized by 1H-NMR, 13C-NMR and FT-
IR spectroscopy.
EXPERIMENTAL SECTION
General: All substrates and reagents were purchased from
Selected Compounds: 1,1-Diacetoxy-1-phenyl methane
(Table 1, entry 1)
commercially sources with the best quality and used without fur-
1
ther purification. IR and H NMR spectra were recorded on
1H-NMR (CDCl3): d 2.14 (s, 6H), 7.41-7.43 (Ar, 3H),
7.52-7.55 (Ar, 2H), 7.69 (s, 1H) ppm; 13C-NMR (CDCl3): d 20.85,
89.67, 126.65, 128.58, 129.74, 135.40, 169.79; IR (KBr) n =
3021, 1761, 1373, 1243, 1216, 1009, 767 cm-1. 1,1-Diacetoxy-1-
(4-bromoyphenyl)methane (Table 1, entry 2): 1H-NMR
(CDCl3): d 2.11 (s, 6H), 7.37-7.40 (Ar, 2H), 7.51-7.54 (Ar, 2H),
7.62 (s, 1H) ppm; 13C-NMR (CDCl3): d 20.78, 89.05, 123.90,
128.40, 131.76, 134.46, 168.64; IR (KBr) n = 3025, 1764, 1373,
1236, 1208, 1070, 1012, 758 cm-1. 1,1-Diacetoxy-1-(4-nitro-
phenyl)methane (Table 1, entry 7): 1H-NMR (CDCl3): d 2.16 (s,
6H), 7.70 (Ar, 2H), 7.73 (s, 1H), 8.27 (Ar, 2H) ppm; 13C-NMR
(CDCl3): d 20.74, 88.30, 123.84, 127.86, 141.87, 148.61, 158.55;
IR (KBr) n = 3033, 1759, 1367, 1239, 1208, 1067, 1007, 812 cm-1.
1,1-Diacetoxy-1-(4-methoxyphenyl)methane (Table 1, entry
9): 1H-NMR (CDCl3): d 2.06 (s, 6H), 3.75 (s, 3H), 6.70 (Ar, 2H),
PerkinElmer FT-IR RXI, 300 MHz Bruker spectrometers, respec-
tively. The products were characterized by their 1H NMR, 13C
NMR or IR spectra and comparison with authentic samples (melt-
ing points). Organic layers were dried over anhydrous sodium
sulfate. All yields referred to isolated pure products. TLC was ap-
plied for the purity determination of substrates, products and re-
action monitoring over silica gel 60 F254 aluminum sheet.
Reductive-acylalation of benzaldehyde with NaBH4/
DOWEX(R)50WX4/Ac2O system, A typical procedure: In a
round-bottomed flask (5 mL) equipped with a magnetic stirrer, a
mixture of benzaldehyde (0.106 g, 1 mmol), Ac2O (0.5 mL) and
DOWEX(R)50WX4 (0.5 g) was prepared. Then the NaBH4
(0.036 g, 1 mmol) was added to the reaction mixture and stirred at
room temperature. TLC monitored the progress of the reaction
942
www.jccs.wiley-vch.de
© 2014 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
J. Chin. Chem. Soc. 2014, 61, 940-944

JOURNAL OF THE CHINESE
CHEMICAL SOCIETY
Fast Preparation of gem-Diacetates from Aldehydes
7.43 (Ar, 2H), 7.61 (s, 1H), ppm; 13C-NMR (CDCl3): d 20.47,
55.08, 89.63, 113.79, 128.01, 131.86, 160.49, 168.72; IR (KBr) n
= 3018, 1738, 1600, 1367, 1259, 1160, 1027, 833 cm-1. 1,1-Di-
acetoxy-1-(2-metoxyphenyl)methane (Table 1, entry 11): 1H-
NMR (CDCl3): d 2.10 (s, 6H), 3.82 (s, 3H), 6.90 (Ar, 1H), 6.98
(Ar, 1H), 7.34 (Ar, 1H), 7.49 (Ar, 1H), 8.03 (s, 1H), ppm; 13C-
NMR (CDCl3): d 20.69, 55.52, 85.54, 110.88, 120.37, 123.72,
126.78, 130.84, 156.89, 168.44; IR (KBr) n = 3016, 1761, 1602,
1372, 1220, 1005, 764 cm-1. 1,1-Diacetoxy-1-(4-methylphen-
12679.
5. (a) Mowry, D. T. J. Am. Chem. Soc. 1950, 72, 2535. (b)
Merten, R.; Muller, G. Angew. Chem. 1962, 74, 866.
6. (a) Trost, B. M.; Vercauteran, J. Tetrahedron Lett. 1985, 26,
131. (b) Trost, B. M.; Lee, C. B.; Weiss, J. M. J. Am. Chem.
Soc. 1995, 117, 7247. (c) Sandberg, M.; Sydnes, L. K. Org.
Lett. 2000, 2, 687.
7. (a) Kula, J. Pol. Pat. PL 143: 824, 1988; (Chem. Abstr. 112,
216290y). (b) Trost, B. M.; Lee, C. J. Am. Chem. Soc. 2001,
123, 12191.
8. Reddy, A. V.; Ravinder, K.; Reddy, V. L. N.; Ravikanth, V.;
Yenkateswarlu, Y. Synth. Commun. 2003, 33, 1531.
9. Bandgar, B. P.; Makone, S. S.; Kulkarni, S. P. Monatsh.
Chem. 2000, 131, 417.
1
yl)methane (Table 1, entry 13): H-NMR (CDCl3): d 2.12 (s,
6H), 2.38 (s, 3H), 7.23 (Ar, 2H), 7.43 (Ar, 2H), 7.66 (s, 1H), ppm;
13C-NMR (CDCl3): d 20.86, 21.28, 89.77, 126.60, 129.25,
132.59, 139.78, 168.80; IR (KBr) n = 3033, 1759, 1367, 1239,
1067, 1039, 812 cm-1. 1,1-Diacetoxy-1-(cinnamyl)methane
(Table 1, entry 14): 1H-NMR (CDCl3): 2.13 (s, 6H), 6.22 (dd, J =
15 Hz, 6 Hz, 1H), 6.82 (d, J = 15 Hz, 1H), 7.27-7.44 (m, 5H), 7.37
(d, J =6 Hz, 1H) ppm; 13C-NMR (CDCl3): d 20.90, 89.71, 121.65,
127.00, 128.66, 128.83, 135.09, 135.60, 168.70; IR (KBr) n =
3024, 1762, 1373, 1243, 1216, 1001, 756, cm-1.
10. Li, T. S.; Zhang, Z. H.; Gao, Y. J. Synth. Commun. 1998, 28,
4655.
11. (a) Kumar, P.; Hegde, V. R.; Kumar, T. P. Tetrahedron Lett.
1995, 36, 601. (b) Pereira, C. B.; Gigante, M. J.; Marcelo-
Curto, H.; Carreyre, G.; Perot, G.; Guisnet, M. Synthesis
1995, 1077. (c) Ballini, R.; Bordoni, M.; Bosica, G.; Maggi,
R.; Sartori, G. Tetrahedron Lett. 1998, 39, 7587.
12. Olah, G. A.; Mehrotra, A. K. Synthesis 1982, 962.
13. Jin, T. S.; Du, G. Y.; Li, T. S. Ind. J. Chem., Sect. B 1998, 939.
14. Wang, C.; Li. M. Synth. Commun. 2002, 32, 3469.
15. Gowravaram, S.; Abraham, S.; Ramalingam, T.; Yadav, J. S.
J. Chem. Res. (S) 2002, 3, 144.
CONCLUSION
In this investigation, we have shown that the NaBH4/
DOWEX(R)50WX4/Ac2O system is suitable for the reduc-
tive-acylalation of a variety of aldehydes to their corre-
sponding gem-diacetates in high to excellent yields. Re-
duction reactions were carried out with 1 molar equivalents
of NaBH4 and Ac2O (0.5 mL) in the presence of 0.5 g
DOWEX(R)50WX4 at room temperature. High efficiency
of the reductions, shorter reaction times and easy work-up
procedure makes as an attractive new protocol for reduc-
tive-acylalation of aldehydes and it could be a useful addi-
tion to the present methodologies.
16. Deka, N.; Borah, R.; Kalita, D. J.; Sarma, J. C. J. Chem.
Res.(S) 1998, 94.
17. Agarwal, V. K.; Fonquerna, S. S.; Vennall, G. P. Synlett 1998,
849.
18. Deka, N.; Kalita, D. J.; Borah, R.; Sarma, J. C. J. Org. Chem.
1997, 62, 1563.
19. Karimi, B.; Seradj, H.; Ebrahimian, R. G. Synlett 2000, 623.
20. Michie, J. K.; Miller, J. A. Synthesis 1981, 824.
21. Gregory, M. J. J. Chem. Soc. B 1970, 1201.
22. Chandra, K. L.; Saravanan, P.; Singh, V. K. Synlett 2000,
359.
23. Sumida, N.; Nishioka, K.; Sato, T. Synlett 2001, 12, 1921.
24. Jin, T. S.; Sun, G.; Li, Y. W.; Li, T. S. Green Chem. 2002, 4,
255.
ACKNOWLEDGMENTS
The authors gratefully appreciated the financial sup-
port of this work by the research council of Islamic Azad
University branch of Mahabad.
25. Yadav, J. S.; Reddy, B. V. S.; Srinivas, Ch. Synth. Commun.
2002, 32, 2169.
26. Roy, S. C.; Banerjee, B. Synlett 2002, 1677.
27. Karimi, B.; Maleki, J. J. Org. Chem. 2003, 68, 4951.
28. Ranu, B. C.; Dutta, J.; Das, A. Chem. Lett. 2003, 32, 366.
29. Firouzabadi, H.; Iranpoor, N.; Nowrouzi, F.; Amani, K. Tet-
rahedron Lett. 2003, 44, 3951.
REFERENCES
1. (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Or-
ganic Synthesis, 3rd Ed.; Wiley-VCH: New York, 1999; p
306. (b) Gregory, M. J. J. Chem. Soc. (B) 1970, 1201.
2. Frick, J. G.; Harper, Jr., R. J. J. Appl. Polymer Sci. 1984, 29,
1433.
30. Smitha, G.; Reddy, Ch.S. Tetrahedron 2003, 59, 9751.
31. Aggen, D. H.; Hayes, Arnold, J. N.; Hayes, P. D.; Smoter, N.
J.; Mohan, R. S. Tetrahedron 2004, 60, 3675.
32. Carrigan, M. C.; Eash, K. J.; Oswald, M. C.; Mohan, R. S.
Tetrahedron Lett. 2001, 42, 8133.
3. Banks, R. E.; Miller, J. A.; Nunn, M. J.; Stanley, P.; Weakley,
T. J. R.; Ullah, Z. J. Chem Soc. Perkin Trans. 1. 1981, 1096.
4. (a) Sandberg, M.; Sydnes, L. K. Tetrahedron Lett. 1998, 39,
6361. (b) Sydnes, L. K.; Sandberg, M. Tetrahedron 1997, 53,
33. Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O.;
Nocchetti, M. Tetrahedron Lett. 2002, 43, 2709.
J. Chin. Chem. Soc. 2014, 61, 940-944
© 2014 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.jccs.wiley-vch.de
943

Article
Asl and Setamdideh
34. Kumar, S.; Saini, A.; Sandhu, J. A. Arkivok 2007, 14, 27.
35. Sun, P.; Hu, Z. J. Chem. Res. 2005, 10, 659.
36. Palacios-Grijalva, L. N.; Cruz-González, D. Y.; Lomas-
Romero, L.; González-Zamora, E.; Ulibarri, G.; Negrón-
Silva, G. E. Molecules 2009, 14, 4065.
48. Ziyaei, A.; Azizi, N.; Saidi, M. R. J. Mol. Catal. A: Chem.
2005, 238, 138.
49. Kumar, R.; Thilagavathi, R.; Gulhane, R.; Chakraborti, A.
K. J. Mol. Catal. A: Chem. 2006, 250, 226.
50. Hajipour, A. A.; Khazdooz, L.; Ruoho, A. E. Catal. Com-
mun. 2008, 9, 89.
37. Ghorbani-Vaghei, R.; Amiri, M.; Moshfeghifar, N.; Veisi,
H.; Akbari Dadamahaleh, S. J. Iran. Chem. Soc. 2009, 6,
754.
51. Setamdideh, D.; Rafigh, M. E-J. Chem. 2012, 4, 2338.
52. Setamdideh, D.; Rahmatollahzadeh, M. J. Mex. Chem. Soc.
2012, 56, 169.
38. Shirini, F.; Mamaghani, M.; Mostashari-Rad, T.; Abedini,
M. Bull. Korean Chem. Soc. 2010, 31, 2399.
53. Setamdideh, D.; Ghahremani, S. S. Afr. J. Chem. 2012, 65,
91.
39. Mirjalili, B. F.; Zolfigol, M. A.; Bamoniri, A.; Sheikhana, N.
J. Chin. Chem. Soc. 2006, 53, 955.
54. Setamdideh, D.; Khezri, B.; Rahmatollahzadeh, M. J. Serb.
Chem. Soc. 2013, 78, 1.
40. Zhang, X.; Li, L.; Zhang, G. Green Chem. 2003, 5, 646.
41. Dalpozzo, R.; Nino, A. D.; Maiuolo, L.; Nardi, M.;
Procopio, A.; Russo, B.; Tagarelli, A. Arkivoc 2006, 6, 181.
42. Shelke, K.; Sapkal, S.; Kategaonkar, A.; Shingate, B.;
Shingare, M .S. S. Afr. J. Chem. 2009, 62, 109.
43. Negrón, E. E.; Palacios, L. N.; Angeles, D.; Lomas, L.;
Gaviño, R. J. Mex. Chem. Soc. 2005, 49, 252.
55. Mohamadi, M.; Setamdideh, D.; Khezri, B. Org. Chem.
Inter. 2013, 2, doi:10.1155/2013/127585.
56. Setamdideh, D.; Khaledi, L. S. Afr. J. Chem. 2013, 66, 150.
57. Setamdideh, D.; Hasani, S.; Noori, S. J. Chin. Chem. Soc.
2013, 60, 1267.
58. Setamdideh, D.; Khezri, B.; Esmaeilzadeh, S. J. Chin. Chem.
Soc. 2012, 59, 1119.
44. Heravi, M. M.; Bakhtiari, K.; Taheri, S.; Oskooie, H. A.
Green Chem. 2005, 7, 867.
59. Setamdideh, D.; Khezri, B.; Alipouramjad, A. J. Chin.
Chem. Soc. 2013, 60, 590.
45. Pourmosavi, S. A.; Zinati, Z. Turk. J. Chem. 2009, 33, 385.
46. Yin, L.; Zhang, Z. H.; Wang, Y. M.; Pang, M. L. Synlett 2004,
10, 1727.
60. Sofighaderi, S.; Setamdideh, D. Orient. J. Chem. 2013, 29,
1135.
47. Khan, A. T.; Choudhury, L. H.; Ghosh, S. J. Mol. Catal. A:
Chem. 2006, 255, 230.
61. Setamdideh, D.; Sepehraddin, F. J. Mex. Chem. Soc. 2014,
58, 22-26.
944
www.jccs.wiley-vch.de
© 2014 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
J. Chin. Chem. Soc. 2014, 61, 940-944