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Table 5 Comparison of efficiency of HNTf2 with reported catalytic methods under solvent-free conditions
Entry
Conditions
Yield (%)
Ref.
1
2
3
4
5
6
7
8
120 ꢀC, 3.5–7 h, H14[NaP5W30O110
120 ꢀC, 4–6 h, HClO4/SiO2
]
50–98
68–88
70–94
48–61
82–93
58–86
51–96
60–86
80–95
82–96
81–96
39
40
41
42
13a
20
17
22
120 ꢀC, 15–120 min, BaCl2/nano-SiO2
120 ꢀC, 6 h, I2 (20 mol%)
120 ꢀC, 1.5–3.5 h, [HO3S(CH2)4mim]HSO4 (20 mol%)
130 ꢀC, 4–7.5 h, wet TCT (5 mol%)
120 ꢀC, 4–7 h, DPAT (2 mol%)
130 ꢀC, 1–6 h, without catalyst
9
10
11
110 ꢀC, 5–9 min, MW, without catalyst
110 ꢀC, 80–150 min, n-TSA
43
19
80 ꢀC, 30–60 min, HNTf2 (1 mol%)
This work
TLC (petroleum ether : ethyl acetate ¼ 7 : 3, v/v). Aer comple-
9 S. Mahernia, M. Adib, M. Mahdavi and M. Nosrati,
Tetrahedron Lett., 2014, 55, 3844.
tion, the reaction mixture was poured in ice water (5 mL) and
the precipitated solid was collected by ltration, washed with 10 M. Adib, N. Ayashi and P. Mirzaei, Synlett, 2016, 27, 417.
distilled water (20 mL) and dried. The crude product was 11 H. Zhang, J. Shen, G. Cheng, B. Wu and X. Cui, Asian J. Org.
recrystallized from 95% ethanol (5 mL) to give the corre-
Chem., 2018, 7, 1089.
sponding pure product. All the products were characterized by 12 Y. M. Ren, Z. Zhang and S. Jin, Synth. Commun., 2016, 46,
1H NMR and 13C NMR spectroscopy.
528.
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Conflicts of interest
There are no conicts to declare.
14 N. Montazeri and S. Mahjoob, Chin. Chem. Lett., 2012, 23,
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Acknowledgements
The authors gratefully acknowledge the nancial support
provided by Shaanxi Key Laboratory for Phytochemistry
(17JS008) and Baoji University of Arts and Sciences (No.
ZK14008).
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5162 | RSC Adv., 2019, 9, 5158–5163
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