Ple Na es we dJ oo u nr no at l ao df jCu hs et mm i as tr rgy ins
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packed column of Restek capillary SE-54. The oxidised products were LY19B010001), the Government of Zhejiang Province (Qianjiang
DOI: 10.1039/D0NJ03776A
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isolated and characterized by H and C NMR spectra recorded on Professorship for XL), Jiaxing University (Summit Program of Jiaxing
Bruker NMR (400 MHz) instrument in CDCl University for Leading Talents) and Municipal Government of Jiaxing
.2 Procedures for the preparation of NH -Y, Cu -Y and Cu -Y (SS) for supporting this work.
zeolites
NH
+-Y zeolite was prepared by mixing an aqueous solution of NH
100 mL, 10%) into the suspension of NaY zeolite (5 g) in 100 mL
3
.
+
II
I
4
4
4
4
Cl
Notes and references
(
deionised water and kept for stirring at 70 °C for 12 hours for ion 1. J. Habermann, S. V. Ley and J. S. Scott, J. Chem. Soc., Perkin Trans.
exchange. The exchange was repeated at least three times. For each 1, 1999, 1253-1256.
time, the zeolite powder was washed repeatedly with distilled water
and then dried. All the cation- exchanged zeolites were activated at
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. C. Parmeggiani and F. Cardona, Green Chem, 2012, 14, 547-564.
. G. Csjernyik, A. H. Éll, L. Fadini, B. Pugin and J.-E. Bäckvall, J. Org.
Chem., 2002, 67, 1657-1662.
II
4
50 °C for 3 h prior to use. Cu -Y zeolite was prepared in the same
4. C. Parmeggiani, C. Matassini and F. Cardona, Green Chem., 2017,
manner by using aqueous solution of Cu(NO
3
)
2
• 3H
2
O (100 mL, 10%). 19, 2030-2050.
I
Cu -Y zeolite was prepared according to the procedure reported by Li 5. M. M. Whittaker and J. W. Whittaker, Biophys. J. 1993, 64, 762-
772.
et al. NH
C for 4 h to obtained HY zeolite. A mixture of CuCl (350 mg, 3.53
mmol) and HY (1 g) were ground in a mortar and then heated in a
4
Y zeolite was first loaded in a furnace and heated at 550
6
. M. F. Semmelhack, C. R. Schmid, D. A. Cortes and C. S. Chou, J. Am.
°
Chem. Soc. 1984, 106, 3374-3376.
7. R. A. Sheldon, I. W. C. E. Arends, G.-J. ten Brink and A. Dijksman,
furnace under flowing nitrogen atmosphere at a heating rate of 10 Acc. Chem. Res. 2002, 35, 774-781.
˗
1
+
°
C min . The ion-exchange of Cu(I) in solid CuCl with H in HY zeolite 8. S. Striegler, N. A. Dunaway, M. G. Gichinga and L. K. Milton,
Tetrahedron 2010, 66, 7927-7932.
occurred at over 300 °C and the maximum ion-exchange rate was
reached at 340 °C with the consequent release of HCl gas. Cu -Y was
prepared at two different temperatures via heating the mixture of
CuCl/HY at 350 °C for 15 h or 450 °C for 6 h under nitrogen Iwabuchi, Angew. Chem. Int. Ed. 2014, 53, 3236-3240.
atmosphere. After the preparation was over, the Cu -Y was kept in 11. Y. Sasano, N. Kogure, S. Nagasawa, K. Kasabata and Y. Iwabuchi,
vacuum.
9
1
. J. E. Steves and S. S. Stahl, J. Am. Chem. Soc. 2013, 135, 15742-
I
5745.
10. Y. Sasano, S. Nagasawa, M. Yamazaki, M. Shibuya, J. Park and Y.
I
Org. Lett. 2018, 20, 6104-6107.
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2. G. Zhan, W. Zhong, Z. Wei, Z. Liu and X. Liu, Dalton Trans. 2017,
6, 8286-8297.
13. J. M. Hoover and S. S. Stahl, J. Am. Chem. Soc. 2011, 133, 16901-
I
4
.3 Aerobic Oxidation of alcohols using Cu -Y zeolite
I
1
00 mg of freshly prepared Cu -Y zeolite was taken in a reaction tube
(15 mL) containing ethanol (3 mL) as a solvent. A mixture of benzyl 16910.
alcohol (1 mmol) and TEMPO (0.25 mmol, 39 mg) were added 14. A. Dijksman, I. W. C. E. Arends and R. A. Sheldon, Org. Biomol.
Chem. 2003, 1, 3232-3237.
1
1
simultaneously to the reaction tube and stirred at 60 °C for 18 h. The
aliquots of the reaction mixture were used for product analysis at
regular interval by gas chromatographic technique. The retention
times for various compounds were determined by injecting pure Compd. 2019, 799, 279-287.
compounds under identical GC conditions. The yield of benzaldehyde 17. L. Kong, J. Zhao, S. Han, T. Zhang, L. He, P. Zhang and S. Dai, Ind.
was calculated from GC analysis using 1,2-dichlorobenzene (0.1 mL)
as the internal standard. For other substrates, the oxidation reaction
was analogously performed. The yield of products was calculated
from GC data and the oxidation products were identified from GC- 20. H. Wang, W. Fan, Y. He, J. Wang, J. N. Kondo and T. Tatsumi, J.
MS results. For isolation of selected compounds, column Catal. 2013, 299, 10-19.
chromatography was performed on silica gel 60-120 mesh with a
mixture of petroleum ether and ethyl acetate (95:5) solvent as
eluent. In repetitive run, the catalyst was separated by filtration,
5. Z. Liu, Z. Shen, N. Zhang, W. Zhong and X. Liu, Catal. Lett. 2018,
48, 2709-2718.
16. N. Ghalavand, M. M. Heravi, M. R. Nabid and R. Sedghi, J. Alloys
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8. R. J. Kalbasi, A. A. Nourbakhsh and M. Zia, J. Inorg. Organomet.
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19. W. Liu, J. Yang and J. Cai, Res. Chem. Intermed. 2019, 45, 549-561.
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1. Z. Wei, S. Ru, Q. Zhao, H. Yu, G. Zhang and Y. Wei, Green Chem.
019, 21, 4069-4075.
2. A. Dhakshinamoorthy, M. Alvaro and H. Garcia, ACS Catal, 2011,
1, 48-53.
followed by solvent evaporation under reduced pressure. The 23. Y.-Z. Chen, R. Zhang, L. Jiao and H.-L. Jiang, Coord. Chem. Rev.
recovered catalyst was thoroughly washed with ethyl acetate and 2018, 362, 1-23.
water. Then it was dried and reactivated at 350 °C for 4 h under N
atmosphere before next run.
2
3
2
4. B. R. Kim, J. S. Oh, J. Kim and C. Y. Lee, B. Korean. Chem. Soc. 2015,
6, 2799-2800.
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Shi, ACS Appl. Nano Mater. 2019, 2, 4435-4442.
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Conflicts of interest
There are no conflicts to declare
186.
2
7. X. Feng, P. Lv, W. Sun, X. Han, L. Gao and G. Zheng, Catal.
Commun. 2017, 99, 105-109.
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Acknowledgements
The authors would like to thank the National Natural Science
Foundation of China (Grant no. 21571083), the Natural Science 30. I. Ibrahem, M. N. Iqbal, O. Verho, A. Eivazihollagh, P. Olsén, H.
Foundation of Zhejiang Province (Grant no. LY18B010007, Edlund, C.-W. Tai, M. Norgren and E. V. Johnston, ChemNanoMat,
2018, 4, 71-75.
29. X. Zhang, W. Dong, Y. Luan, M. Yang, L. Tan, Y. Guo, H. Gao, Y.
Tang, R. Dang, J. Li and G. Wang, J. Mater. Chem. A. 2015, 3, 4266-
4
273.
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