ChemSusChem
10.1002/cssc.201800587
FULL PAPER
Langmuir, 2010, 26, 16291-16298; c) J. J. Tan, J. L. Cui, G. Q. Ding, T.
S. Deng, Y. L. Zhu, Y. W. Li, Catal. Sci. Technol. 2016, 6, 1469-1475.
S. Baj, R. Słupska, A. Chrobok, A. Drożdż, J. Mol. Catal. A, 2013, 376,
General procedures of expanding the substrates and the
data of NMR.
[
4]
5]
6
The substrate (1 mmol) and 1.0 mol% W(OTf) were added in
120-126.
a 10 mL Schleck tube equipped with a magnetic stirrer at 500
[
M. Markiton, A. Chrobok, K. Matuszek, K. R. Seddonb, M. Swadźba-
Kwaśny, RSC Adv. 2016, 6, 30460-30467.
rpm. The reaction mixture was stirred for 10 h (or 24 h) at 180
oC in 1 mL pre-dried [EMIM]OTf under Ar atmosphere. After the
[6]
a) U. G. Hong, S. Hwang, J. G. Seo, J. Yi, I. K. Song, Catal Lett, 2010,
138, 28-33; b) B. Tapin, F. Epron, C. Especel, B. K. Ly, C. Pinel, M.
reaction, the reaction mixture was diluted with ethyl acetate
then washed with saturated NaCl solution more than 10 times
until the aqueous phase was clear. The organic parts were
Besson, ACS Catal. 2013, 3, 2327-2335.
[7]
a) Yu. N. Ogibin, É. I. Troyanskii, V. I. Kadentsev, E. D. Lubuzh, O. S.
Chizhov, G. I. Nikishin, Russ Chem Bull, 1981, 30, 830-834; b) X. Q.
Tan, T. Song, Z. T. Wang, H. Chen, L. Cui and C. Z. Li, Org. Lett.,
combined, dried over anhydrous Na
2
SO
4
,
filtered and
2
017, 19, 1634-1637.
Y. B. Zhou, L. K. Woo, R. J. Angelici, Appl. Catal. A, 2007, 333, 238-
44.
S. Akula, P. P. Kumar, R. B.N. Prasad, S. Kanjilal, Tetrahedron Lett.
012, 53, 3471-3473.
concentrated to obtain the target compound. Then the crude
compound was purified by a short silica column with gradient
elution (ethyl acetate : petroleum ether = 1:5 - 1:50). The
solvent was evaporated and the desired product was obtained.
All the products were characterized with NMR and the spectrum
data were listed in Supporting Information.
[
8]
9]
2
[
2
[10] a) N. Ajellal, J. F. Carpentier, C. Guillaume, S. M. Guillaume, M. Helou,
V. Poirier, Y. Sarazin, A. Trifonov, Dalton Trans. 2010, 39, 8363-8376;
b) N. Nomura, A. Taira, T. Tomioka, M. Okada, Macromolecules, 2000,
General procedures of recycle of [EMIM]OTf.
[
528.
6
ε-Caprolactone (1 mmol) and 1.0 mol% W(OTf) were added
7
in a 10 mL Schleck tube equipped with a magnetic stirrer at 500
[12] A. Skrobiszewski, W. Gładkowski, P. Walczak, A. Gliszczyńska, G.
o
rpm. The reaction mixture was stirred for 10 h at 180 C in 1 mL
Maciejewska, T. Klejdysz, J. Nawrot, C. Wawrzeńczyk, J. Chem. Sci.
pre-dried [EMIM]OTf under Ar atmosphere. The contents of γ-,
δ- and ε-caprolactone were determined by GC analysis with
biphenyl as the internal standard. After that, the solution was
diluted with ethyl acetate and extracted with pure water until the
aqueous phase was clear. Combined the aqueous layer then
vacuum evaporated. Finally, the residue ([EMIM]OTf) was dried
through oil pump to remove the trace water and for the next use.
2
015, 127, 687-699.
[13] a) Z. R. Zhang, J. L. Song, B. X. Han, Chem. Rev. 2017, 117, 6834-
880; b) C. Z. Li, X. C. Zhao, A. Q. Wang, G. W. Huber, T. Zhang,
6
Chem. Rev. 2015, 115, 11559-11624; c) L. Lai, Y. G. Zhang,
ChemSusChem, 2010, 3, 1257-1259; d) Y. C. Hu, N. Li, G. Y. Li, A. Q.
Wang, Y. Cong, X. D. Wang, T. Zhang, ACS Catal. 2017, 7, 2576-
2582.
[14] a) H. J. Song, J. Deng, M. S. Cui, X. L. Li, X. X. Liu, R. Zhu, W. P. Wu ,
Y. Fu, ChemSusChem, 2015, 8, 4250-4255; b) Y. G. Zhang, L. W.
Chen, T. Lu, Adv. Synth. Catal. 2011, 353, 1055-1060.
[
[
[
15] X. L. Li, K. Zhang, J. L. Jiang, R. Zhu, W. P. Wu, J. Deng, Y. Fu,
Conflicts of interest
Green Chem. 2018, 20, 362-368.
There are no conflicts to declare.
16] K. Zhang, X. L. Li, S. Y. Chen, H. J. Xu, J. Deng, Y. Fu,
ChemSusChem, 2018, 11, 726-734.
17] a) Z. Li, R. S. Assary, A. C. Atesin, L. A. Curtiss, T. J. Marks, J. Am.
Chem. Soc. 2014, 136, 104-107; b) T. L. Lohr, Z. Li, R. S. Assary, L. A.
Curtiss, T. J. Marks, Energy Environ. Sci. 2016, 9, 550-564.
18] J. S. Gou, Z. P. Wang, C. Li, X. D. Qi, V. Vattipalli, Y. T. Cheng, G.
Huber, W. C. Conner, P. J. Dauenhauer, T. J. Mountziaris, W. Fan,
Green Chem. 2017, 19, 3549-3557.
Acknowledgements
This work was supported by the NSFC (21732006, 21572212,
[
21402181), MOST (2017YFA0303502), CAS (YZ201563),
FRFCU (WK3530000004) and PCSIRT. The authors thank the
Hefei Leaf Biotech Co., Ltd. and Anhui Kemi Machinery
Technology Co., Ltd. for free samples and equipment that
benefited our ability to conduct this study.
[19] G. Q. Lv, H. L. Wang, Y. X. Yang, X. Li, T. S. Deng, C. M. Chen, Y. L.
Zhu, X. L. Hou, Catal. Sci. Technol. 2016, 6, 2377-2386.
[
20] a) Y. F. Ma, G. Y. Xu, H. Wang, Y. X. Wang, Y. Zhang, Y. Fu, ACS
Catal. 2018, 8, 1268−1277; b) J. Fujita, A. E. Martell, K. Nakamoto, J
Chem Phys, 1962, 36, 339-345; c) K. G. Severin, J. S. Ledford, Chem.
Mater. 1994, 6, 890-898; d) M. Rogojerov, G. Keresztury, B. Jordanov,
Spectrochimica Acta, Part A, 2005, 61,1661-1670; e) G. L. Dimas-
Rivera, J. R. de la Rosa, C. J. Lucio-Ortiz, J. A. De los Reyes Heredia,
V. G. González, T. Hernández, Materials, 2014, 7, 527-541.
Keywords: γ-lactones • metal triflates • ionic liquid • ring
contraction • rearrangement
[
1]
2]
a) L. J. Gooβen, D. M. Ohlmann, M. Dierker, Green Chem. 2010, 12,
[21] a) H. B. Zhao, J. E. Holladay, H. Brown, Z. C. Zhang, Science, 2007,
1
1
1
97-200; b) M. de Lꢀsꢀleuc, S. K. Collins, ACS Catal. 2015, 5, 1462-
316, 1597-1600; b) A. P. Abott, G. Capper, D. L. Davies, H. L. Munro,
467; c) L. Coulombel, E. Duñach, Synth. Commun. 2005, 35, 153-
R. K. Rasheed, V. Tambyrajah, Chem Commun. 2001, 0, 2010-2011.
60.
[
a) S. W. Chang, C. Y. Hung, H. H. Liu, B. J. Uang, Tetrahedron:
Asymmetry, 1998, 9, 521-529; b) D. Romano, M. Contente, T. Granato,
W. Remelli, P. Zambelli, F. Molinari, Monatsh Chem, 2013, 144, 735-
737; c) C. Zhang, L. F.Chen, H. Y. Cheng, X. D. Zhu, Z. W. Qi, Catal
Today, 2016, 276, 55-61.
[3]
a) J. C. Serrano-Ruiz, D. Wang, J. A. Dumesic, Green Chem. 2010, 12,
574-577; b) J. Q. Bond, D. M. Alonso, R. M. West, J. A. Dumesic,
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