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Green Chemistry
Page 5 of 7
DOI: 10.1039/C5GC02761F
Journal Name
ARTICLE
In a typical reaction, a Schlenk flask (10 mL) equipped with a
J. M. McKay and S. T. Nguyen, Tetrahedron Lett., 2004, 45,
2
023.
CO
2
balloon was bubbled with CO
2
to evacuate air. Then
(0.0500 g, 0.25
6
7
(
a
) Y. W. Ren, Y. C. Shi, J. X. Chen, S. R. Yang, C. R. Qi
styrene epoxide (5 mmol, 0.6008 g), CaBr
2
and H. F. Jiang, RSC Adv., 2013, 3, 2167; (b) F. W. Li, C. G.
mmol), DBU (0.0380 g, 0.25 mmol) and DMF (1 mL) were
added successively. The flask was placed in an oil bath, and
Xia, L. W. Xu, W. Sun and G. X. Chen, Chem. Commun
.
2003, 2042.
o
stirred at 100 C for 12 h. For low boilingꢀpoint epoxides (2a,
(
a) C. Maeda, T. Taniguchi, K. Ogawa, and T. Ema, Angew.
Chem. Int. Ed., 2015, 54, 134; ( ) M. Taherimehr, A.
b
3
a, 11a), the reaction was carried out in a stainless steel
autoclave (25 mL) equipped with a gauge to measure the
pressure of the system. Under this circumstance, a CO pressure
5 bar for 2a and 3a) is necessary to provide enough CO . After
reaction, the reactor was cooled to 0 C and excess of CO was
vented. Then biphenyl (0.4624 g, mmol) or 1,3,5ꢀ
Decortes, S. M. AlꢀAmsyar, W. Lueangchaichaweng, C. J.
Whiteoak, E. C. EscuderoꢀAda´n, A. W. Kleij and P. P.
Pescarmona, Catal. Sci. Technol., 2012, 2, 2231.
2
(
2
8
9
1
(
a
) A. Buchard, M. R. Kember, K. G. Sandeman and C. K.
o
Williams, Chem. Commun., 2011, 47, 212; ( ) C. J.
b
2
Whiteoak, E. Martin, M. M. Belmonte, J. BenetꢀBuchholz
3
and A. W. Kleij, Adv. Synth. Catal., 2012, 354, 469.
trimethoxybenzene (0.0841 g, 0.5 mmol) was added as internal
(
a) H. Zhou, Y. M. Wang, W. Z. Zhang, J. P. Qu and X. B.
1
standard for the analysis of product yields by GC or H NMR.
Lu, Green Chem., 2011, 13, 644; ( ) Y. Kayaki, M.
b
The products were purified by column chromatography and
Yamamoto and T. Ikariya, Angew. Chem. Int. Ed., 2009, 48,
4194.
1
13
characterized by H NMR and C NMR spectra.
0 (
a)
A. M. HardmanꢀBaldwin and A. E. Mattson,
ChemSusChem, 2014, 7, 3275; ( ) M. E. Wilhelm, M. H.
Anthofer, M. Cokoja, I. I. E. Markovits, W. A. Herrmann
b
Computational details
All the calculations were carried out by the density functional
and F. E. Kühn, ChemSusChem, 2014, 7, 1357.
2
4
25
11 (
a
) Z. Z. Yang, Y. N. Zhao, L. N. He, J. Gao and Z. S. Yin,
theory (DFT) method, where GAUSSIAN 09 package was
employed. All the structures reported in this research were
optimized by the M06 method in conjunction with 6ꢀ
Green Chem., 2012, 14, 519; ( ) J. Sun, L. J. Han, W. G.
b
Cheng, J. Q. Wang, X. P. Zhang and S. J. Zhang,
ChemSusChem, 2011, 4, 502.
11++G** basis set. All final structures were confirmed by 12 C. J. Whiteoak, N. Kielland, V. Laserna, E. C. Escuderoꢀ
2
6
3
frequency calculation to be the real minima without any
imaginary frequencies by using the same level of theory. All
length data were in angstroms (Å). Structures were generated
Adán, E. Martin and A. W. Kleij, J. Am. Chem. Soc., 2013,
35, 1228.
3 J. M. Begouin, M. Niggemann, Chem. Eur. J., 2013, 19, 8030;
) S. Harder, Chem. Rev., 2010, 110, 3852.
4 M. Niggemann and M. J. Meel, Angew. Chem. Int. Ed., 2010,
9, 3684.
5 T. Haven, G. Kubik, S. Haubenreisser and M. Niggemann,
Angew. Chem. Int. Ed., 2013, 52, 4016.
6 S. Kobayashi and Y.Yamashita, Acc. Chem. Res., 2011, 44,
1
1
1
1
1
(b
2
5
using CYLview.
4
Acknowledgements
We are grateful to the National Natural Sciences Foundation of
58.
China, the Specialized Research Fund for the Doctoral Program 17 L. Fu and M. Niggemann, Chem. Eur. J., 2015, 21, 6367.
of Higher Education (20130031110013), the MOE Innovation 18 K. Kossev, N. Koseva and K. Troev, J. Mol. Catal. A: Chem.,
2
003, 194, 29.
Team (IRT13022) of China, the Foundation of State Key
Laboratory of Coal Conversion (Grant No. J16ꢀ17ꢀ902ꢀ2) and
the “111” Project of Ministry of Education of China (project
No.B06005) for financial support.
1
2
9 D. S. Bai, G. J. Wang, F. Ma, J. G. Wang, K. Wang and Z. J.
Yang, Appl. Organometal. Chem., 2014, 28, 814.
0 (
(
a
b
) Y. P. Ren and J. J. Shim, ChemCatChem, 2013, 5, 1344;
) C. D. N. Gomes, O. Jacquet, C. Villiers, P. Thuery, M.
Ephritikhine and T. Cantat, Angew. Chem. Int. Ed., 2012, 51,
87; ( ) Y. Kayaki, M. Yamamoto and T. Ikariya, J. Org.
Chem., 2007, 72, 647; ( ) R. L. Paddock and S. T. Nguyen, J.
1
c
d
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