(n = 5), 563.3 (n = 6), 607.3 (n = 7), 651.4 (n = 8), 697.4 (n = 9),
739.4 (n = 10), 785.4 (n = 11), 827.4 (n = 12) [M-Br]+.
M. Jorgensen and F. C. Krebs, Energy Environ. Sci., 2010, 3, 43–81;
(f) I. Omae, Catal. Today, 2006, 115, 33–52.
3 Application of cyclic carbonates: (a) M. Yoshida and M. Ihara,
Chem.–Eur. J., 2004, 10, 2886–2893; (b) J. H. Clements, Ind. Eng.
Chem. Res., 2003, 42, 663–674; (c) J. Sun, S.-i. Fujita and M. Arai,
J. Organomet. Chem., 2005, 690, 3490–3497; (d) T. Sakakura and K.
Kohno, Chem. Commun., 2009, 1312–1330; (e) W.-L. Dai, S.-L. Luo,
S.-F. Yin and C.-T. Au, Appl. Catal., A, 2009, 366, 2–12.
4 M. North, R. Pasquale and C. Young, Green Chem., 2010, 12, 1514–
1539.
5 Advantages of ionic liquids: (a) Z. Z. Yang, L. N. He, C. X. Miao
and S. Chanfreau, Adv. Synth. Catal., 2010, 352, 2233–2240; (b) J.
Sun, J. Ren, S. Zhang and W. Cheng, Tetrahedron Lett., 2009, 50,
423–426; (c) Y. Zhou, S. Hu, X. Ma, S. Liang, T. Jiang and B. Han,
J. Mol. Catal. A: Chem., 2008, 284, 52–57; (d) J. Sun, S. Zhang, W.
Cheng and J. Ren, Tetrahedron Lett., 2008, 49, 3588–3591; (e) Y. J.
Kim and R. S. Varma, J. Org. Chem., 2005, 70, 7882–7891; (f) J.
Palgunadi, O. S. Kwon, H. Lee, J. Y. Bae, B. S. Ahn, N.-Y. Min and
H. S. Kim, Catal. Today, 2004, 98, 511–514; (g) F. Li, L. Xiao, C. Xia
and B. Hu, Tetrahedron Lett., 2004, 45, 8307–8310; (h) J. Sun, S.-i.
Fujita, F. Zhao and M. Arai, Green Chem., 2004, 6, 613–616; (i) H.
Kawanami, A. Sasaki, K. Matsui and Y. Ikushima, Chem. Commun.,
2003, 896–897; (j) J. Peng and Y. Deng, New J. Chem., 2001, 25, 639–
641; (k) J. Sun, L. Han, W. Cheng, J. Wang, X. Zhang and S. Zhang,
ChemSusChem, 2011, 4, 502–507; (l) H. S. Kim, J. J. Kim, H. Kim
and H. G. Jang, J. Catal., 2003, 220, 44–46.
BrDBUPEG150DBUBr. Brown oil; 1H NMR (D2O,
400 MHz) d 3.67–3.73 (m, 12H), 3.60–3.62 (m, 4H), 3.49–3.51
3
3
(m, 8H), 2.83 (d, J = 8.8 Hz, 4H), 2.04 (t, J = 5.2 Hz, 4H),
1.68–1.71 (m, 12H); 13C NMR (D2O, 100.6 MHz) d 167.2, 70.1,
68.0, 54.8, 52.5, 48.9, 47.2, 28.0, 25.4, 22.6, 19.6; ESI-MS calcd
for C24H44Br2N4O2 578.18, found 210.5 [(M–2Br)/2]+, 499.4,
501.4 [M–Br]+.
BrTBDPEG150TBDBr. Yellow oil; 1H NMR (D2O,
3
400 MHz) d 3.68 (s, 6H), 3.48 (t, J = 5.2 Hz, 4H), 3.21–3.39
(m, 18H), 1.93–2.00 (m, 8H); 13C NMR (D2O, 100.6 MHz) d
151.3, 70.0, 68.2, 49.7, 47.4, 47.0, 46.8, 46.4, 38.4, 37.8, 20.6,
20.3, 20.2; ESI-MS calcd for C20H38Br2N6O2 552.14, found
197.3 [(M–2Br)/2]+, 393.3 [M–2Br–H]+, 473.0, 475.0 [M–Br]+.
BrMImPEG150MImBr. Light brown oil; 1H NMR (D2O,
400 MHz) d 7.52 (s, 2H), 7.46 (s, 2H), 4.40 (t, 3J = 4.8 Hz, 4H),
3.89–3.91 (m, 10H), 3.69 (s, 4H); 13C NMR (D2O, 100.6 MHz)
d 136.1, 123.5, 122.5, 69.6, 68.5, 49.0, 35.8; ESI-MS calcd for
C14H24Br2N4O2 438.03, found 140.3 [(M-2Br)/2]+, 359.1, 361.1
[M-Br]+.
6 F. Jutz, J.-M. Andanson and A. Baiker, Chem. Rev., 2011, 111, 322–
353.
7 Z.-Z. Yang, L.-N. He, S.-Y. Peng and A.-H. Liu, Green Chem., 2010,
12, 1850–1854.
8 Cyclic carbonates synthesis under atmospheric CO2 using solvents:
(a) V. Calo´, A. Nacci, A. Monopoli and A. Fanizzi, Org. Lett., 2002, 4,
2561–2563; (b) T. Nishikubo, A. Kameyama, J. Yamashita, M. Tomoi
and W. Fukuda, J. Polym. Sci., Part A: Polym. Chem., 1993, 31, 939–
947; (c) T. Nishikubo, A. Kameyama, J. Yamashita, T. Fukumitsu,
C. Maejima and M. Tomoi, J. Polym. Sci., Part A: Polym. Chem.,
1995, 33, 1011–1017; (d) B. Ochiai and T. Endo, J. Polym. Sci., Part
A: Polym. Chem., 2007, 45, 5673–5678; (e) N. Takeda and S. Inoue,
Bull. Chem. Soc. Jpn., 1978, 51, 3564–3567.
BrDBNPEG150DBNBr. Brown oil; 1H NMR (D2O,
400 MHz) d 3.68–3.73 (m, 12H), 3.59 (s, 4H), 3.45 (s, 4H),
3
3.38 (s, 4H), 3.00 (t, J = 7.2 Hz, 4H), 2.05–2.12 (m, 8H); 13C
NMR (D2O, 100.6 MHz) d 165.1, 70.1, 67.5, 54.3, 52.2, 44.8,
42.2, 30.6, 17.7, 18.0; ESI-MS calcd for C20H36Br2N4O2 522.12,
found 182.5 [(M–2Br)/2]+, 443.3, 445.3 [M–Br]+.
9 Cyclic carbonates synthesis under atmospheric CO2 using cocata-
lysts: (a) K. Kasuga, T. Kato, N. Kabata and M. Handa, Bull. Chem.
Soc. Jpn., 1996, 69, 2885–2888; (b) L. Jin, H. Jing, T. Chang, X. Bu,
L. Wang and Z. Liu, J. Mol. Catal. A: Chem., 2007, 261, 262–266;
(c) T. Fujinami, T. Suzuki, M. Kamiya, S.-i. Fukuzawa and S. Sakai,
Chem. Lett., 1985, 14, 199–200; (d) J. Mele´ndez, M. North and R.
Pasquale, Eur. J. Inorg. Chem., 2007, 3323–3326; (e) M. North and
R. Pasquale, Angew. Chem., Int. Ed., 2009, 48, 2946–2948; (f) A.
Berkessel and M. Brandenburg, Org. Lett., 2006, 8, 4401–4404.
10 K. Motokura, S. Itagaki, Y. Iwasawa, A. Miyaji and T. Baba, Green
Chem., 2009, 11, 1876–1880.
Acknowledgements
This work was financially supported by the National Nat-
ural Science Foundation of China (Grants Nos. 20872073,
21150110105, 21172125), the “111” Project of Ministry of
Education of China (Project No. B06005), and the Committee
of Science and Technology of Tianjin.
Notes and references
11 J. Melendez, M. North and P. Villuendas, Chem. Commun., 2009,
2577–2579.
1 Typical examples for CO2 capture and conversion, see: (a) D. M.
D’Alessandro, B. Smit and J. R. Long, Angew. Chem., Int. Ed.,
2010, 49, 6058–6082; (b) S. Choi, J. H. Drese and C. W. Jones,
ChemSusChem, 2009, 2, 796–854; (c) J. E. Bara, T. K. Carlisle, C.
J. Gabriel, D. Camper, A. Finotello, D. L. Gin and R. D. Noble, Ind.
Eng. Chem. Res., 2009, 48, 2739–2751; (d) J.-L. Wang, C.-X. Miao,
X.-Y. Dou, J. Gao and L.-N. He, Curr. Org. Chem., 2011, 15, 621–
646; (e) L.-N. He, J.-Q. Wang and J.-L. Wang, Pure Appl. Chem.,
2009, 81, 2069–2080; (f) L.-N. He, Z.-Z. Yang, A.-H. Liu and J. Gao,
Advances in CO2 Conversion and Utilization, ed., Y. H. Hu, American
Chemical Society, Washington, DC, 2010, pp. 77–101; (g) Z.-Z. Yang,
Y.-N. Zhao and L.-N. He, RSC Adv., 2011, 1, 545–567.
2 Synthesis of value-added chemicals using CO2 as a feedstock: (a) H.
Arakawa, M. Aresta, J. N. Armor, M. A. Barteau, E. J. Beckman,
A. T. Bell, J. E. Bercaw, C. Creutz, E. Dinjus, D. A. Dixon, K.
Domen, D. L. DuBois, J. Eckert, E. Fujita, D. H. Gibson, W. A.
Goddard, D. W. Goodman, J. Keller, G. J. Kubas, H. H. Kung, J. E.
Lyons, L. E. Manzer, T. J. Marks, K. Morokuma, K. M. Nicholas,
R. Periana, L. Que, J. Rostrup-Nielson, W. M. H. Sachtler, L. D.
Schmidt, A. Sen, G. A. Somorjai, P. C. Stair, B. R. Stults and W.
Tumas, Chem. Rev., 2001, 101, 953–996; (b) T. Sakakura, J.-C. Choi
and H. Yasuda, Chem. Rev., 2007, 107, 2365–2387; (c) M. Aresta and
A. Dibenedetto, Dalton Trans., 2007, 2975–2992; (d) S. N. Riduan
and Y. Zhang, Dalton Trans., 2010, 39, 3347–3357; (e) M. Mikkelsen,
12 Advantages of using PEG in CO2 conversion: (a) D. J. Heldebrant and
P. G. Jessop, J. Am. Chem. Soc., 2003, 125, 5600–5601; (b) J. Zhang, B.
Han, Y. Zhao, J. Li, M. Hou and G. Yang, Chem. Commun., 2011, 47,
1033–1035; (c) N. P. Patel, M. A. Hunt, S. Lin-Gibson, S. Bencherif
and R. J. Spontak, J. Membr. Sci., 2005, 251, 51–57.
13 Y. Du, J.-Q. Wang, J.-Y. Chen, F. Cai, J.-S. Tian, D.-L. Kong and
L.-N. He, Tetrahedron Lett., 2006, 47, 1271–1275.
14 J.-S. Tian, C.-X. Miao, J.-Q. Wang, F. Cai, Y. Du, Y. Zhao and L.-N.
He, Green Chem., 2007, 9, 566–571.
15 X. Dou, J. Wang, Y. Du, E. Wang and L. He, Synlett, 2007, 18,
3058–3062.
16 K. Suzawa, M. Ueno, A. E. H. Wheatley and Y. Kondo, Chem.
Commun., 2006, 4850–4852.
17 CO2 activation through forming carbamate species: (a) E. R. Pe´rez,
M. O. da Silva, V. C. Costa, U. P. Rodrigues-Filho and D. W. Franco,
Tetrahedron Lett., 2002, 43, 4091–4093; (b) T. Endo, D. Nagai, T.
Monma, H. Yamaguchi and B. Ochiai, Macromolecules, 2004, 37,
2007–2009; (c) L. Phan, J. R. Andreatta, L. K. Horvey, C. F. Edie,
A.-L. Luco, A. Mirchandani, D. J. Darensbourg and P. G. Jessop, J.
Org. Chem., 2008, 73, 127–132; (d) F. S. Pereira, E. R. deAzevedo, E.
F. da Silva, T. J. Bonagamba, D. L. da Silva Agost´ıni, A. Magalha˜es,
A. E. Job and E. R. Pe´rez Gonza´lez, Tetrahedron, 2008, 64, 10097–
10106; (e) M. Yoshizawa-Fujita, D. R. MacFarlane, P. C. Howlett
526 | Green Chem., 2012, 14, 519–527
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