A poly(ethylene glycol)-supported quaternary ammonium salt for highly efficient and environmentally friendly chemical fixation of CO2 with epoxides under supercritical conditions

Tetrahedron Letters

Volumn 47, Issue 8, 2006, Pages 1271-1275

  Du, Ya ^a   Wang, Jin Quan ^a   Chen, Jian Yu ^a   Cai, Fei ^a   Tian, Jie Sheng ^a   Kong, De Lin ^a   He, Liang Nian ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Cyclic carbonate; Homogeneous catalyst recycling; Polyethylene glycol; Supercritical CO2; Supported catalyst

Indexed keywords

CARBON DIOXIDE; EPICHLOROHYDRIN; EPOXIDE; ETHER DERIVATIVE; GLYCIDYL PHENYL ETHER; ISOPROPYL GLYCIDYL ETHER; MACROGOL 6000; PROPYLENE CARBONATE; PROPYLENE OXIDE; QUATERNARY AMMONIUM DERIVATIVE; STYRENE OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBOXYLATION; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CYCLOADDITION; RECYCLING; SYNTHESIS;

EID: 30944459438     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.12.077     Document Type: Article

References (66)

1. P.T. Anastas Green Chem. 5 2003 G29
2. P.T. Anastas, and R.L. Lankey Green Chem. 2 2000 289
3. K. Biggadike, R.M. Angell, C.M. Burgess, R.M. Farrel, A.P. Hancock, A.J. Harker, W.R. Irving, C. Ioannou, P.A. Procopiou, R.E. Shaw, Y.E. Solanke, O.M.P. Singh, M.A. Snowden, R.J. Stubbs, S. Walton, and H.E. Weston J. Med. Chem. 43 2000 19
4. A.-A.G. Shaikh, and S. Sivaram Chem. Rev. 96 1996 951
5. D.J. Darensbourg, and M.W. Holtcamp Coord. Chem. Rev. 153 1996 155
6. R.L. Paddock, and S.-B.T. Nguyen J. Am. Chem. Soc. 123 2001 11498
7. J.L. Jiang, F.X. Gao, R.M. Hua, and X.Q. Qiu J. Org. Chem. 70 2005 381
8. H. Kawanami, A. Sasaki, K. Matsui, and Y. Ikushima Chem. Commun. 2003 896
9. N. Kihara, N. Hara, and T. Endo J. Org. Chem. 58 1993 6198
10. J. Sun, S.-I. Fujita, and M. Arai J. Organomet. Chem. 690 2005 3490
11. Y. Du, D.-L. Kong, H.-Y. Wang, F. Cai, J.-S. Tian, J.-Q. Wang, and L.-N. He J. Mol. Catal. A: Chem. 241 2005 233
12. J.W. Huang, and M. Shi J. Org. Chem. 68 2003 6705
13. Y. Du, F. Cai, D.-L. Kong, and L.-N. He Green Chem. 7 2005 518
14. W.N. Sit, S.M. Ng, K.Y. Kwong, and C.P. Lau J. Org. Chem. 70 2005 8583
15. H. Yasuda, L.-N. He, T. Sakakura, and C.-W. Hu J. Catal. 233 2005 119
16. K. Yamaguchi, K. Ebitani, T. Yoshida, H. Yoshida, and K. Kaneda J. Am. Chem. Soc. 121 1999 4526
17. T. Nishikubo, A. Kameyama, J. Yamashita, M. Tomoi, and W. Fukuda J. Polym. Sci., Part A: Polym. Chem. 31 1993 939
18. M. Tu, and R.J. Davis J. Catal. 199 2001 85
19. H. Yasuda, L.-N. He, and T. Sakakura J. Catal. 209 2002 547
20. H. Yasuda, L.-N. He, and T. Sakakura Stud. Surf. Sci. Catal. 145 2003 259
21. X.-B. Lu, Y.-J. Zhang, K. Jin, L.-M. Luo, and H. Wang J. Catal. 227 2004 537
22. M. Aresta, A. Dibenedetto, L. Gianfrate, and C. Pastore J. Mol. Catal. A: Chem. 204-205 2003 245
23. M. Aresta, A. Dibenedetto, L. Gianfrate, and C. Pastore Appl. Catal. A 255 2003 5
24. M. Aresta, and A. Dibenedetto J. Mol. Catal. 182-183 2002 399
25. J. Sun, S.-I. Fujita, F.Y. Zhao, and M. Arai Green Chem. 6 2004 613
26. F. Shi, Q. Zhang, Y. He, and Y. Deng J. Am. Chem. Soc. 127 2005 4182
27. R. Srivastara, D. Srinivas, and P. Ratnasamy J. Catal. 233 2005 1 and references cited therein
28. M. Ramin, J.-D. Grunwaldt, and A. Baiker J. Catal. 234 2005 256
29. D.E. Bergbreiter Chem. Rev. 102 2002 3345
30. D.J. Cole-Hamilton Science 299 2003 1702
31. B. Clapham, T.S. Reger, and K.D. Janda Tetrahedron 57 2001 4637
32. Q.-H. Fan, Y.-M. Li, and A.S.C. Chan Chem. Rev. 102 2002 3385
33. U. Kragl, and T. Dwars Trends Biotechnol. 19 2001 442
34. P. Mastrorilli, and C.F. Nobile Coord. Chem. Rev. 248 2004 377
35. P.L. Osburn, and D.E. Bergbreiter Prog. Polym. Sci. 26 2001 2015
36. E.J. Beckmann J. Supercrit. Fluids 28 2004 121
37. T.J. Dickerson, N.N. Reed, and K.D. Janda Chem. Rev. 102 2002 3325
38. M. Benaglia, A. Puglisi, and F. Cozzi Chem. Rev. 103 2003 3401
39. V.K. Dioumaev, and R.M. Bullock Nature 424 2000 530
40. D. Bradley Science 300 2003 2022
41. U.K. Anyanwu, and D. Venkataraman Green Chem. 7 2005 424
42. S. Kinoshita, F. Shibahara, and K. Nozaki Green Chem. 7 2005 256
43. D.J. Heldebrant, and P.G. Jessop J. Am. Chem. Soc. 125 2003 5600
44. R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, and G. Tocco Org. Lett. 2 2000 1737
45. M.T. Reetz, and W. Wiesenhöfer Chem. Commun. 2004 2750
46. J. Chen, S.K. Spear, J.G. Huddleston, and R.D. Rogers Green Chem. 7 2005 64 and references cited therein
47. S. Chandrasekhar, Ch. Narsihmulu, S.S. Sultana, and N.R. Reddy Chem. Commun. 2003 1716
48. M. Solinas, J. Jiang, O. Stelzer, and W. Leitner Angew. Chem., Int. Ed. 44 2005 2291
49. Z. Hou, N. Theyssen, A. Brinkmann, and W. Leitner Angew. Chem., Int. Ed. 44 2005 1346
50. K. Černovská, M. Kemter, H.-C. Gallmeier, P. Rzepecki, T. Schrader, and B. König Org. Biomol. Chem. 2 2004 1603
51. O.A. Attanasi, L.D. Crescentini, G. Favi, P. Filippone, S. Lillini, F. Mantellini, and S. Santeusanio Org. Lett. 7 2005 2469
52. 2 was synthesized according to the reported procedures: S. Bhattacharya, P.S. Goyal, V.K. Aswal, and S. De J. Phys. Chem. B 102 1998 6152
53. S. Grinberg, and E. Shaubi Tetrahedron 1991 2895
54. G. Wu, Y. Wu, and J.F.W. Keana J. Org. Chem. 52 1987 2571 and Ref. 7b. The experimental procedures and NMR data are given in the Supplementary data.
55. T. Guadagno, and S.G. Kazarian J. Phys. Chem. B 108 2004 13995
56. P. Jessop, D.C. Wyne, S. DeHaai, and D. Nakawatase Chem. Commun. 2000 693 and references cited therein
57. D. Gourgouillon, H.M.N.T. Avelino, J.M.N.A. Fareleira, and M.N. da Ponte J. Supercrit. Fluids 13 1998 177
58. Y.W. Kho, D.C. Conrad, R.A. Shick, and B.L. Knutson Ind. Eng. Chem. Res. 42 2003 6511
59. D.L. Tomasko, H. Li, D. Liu, X. Han, M.J. Wingert, L.J. Lee, and K.W. Koelling Ind. Eng. Chem. Res. 42 2003 6431
60. The enantiomeric excess of (R)-1-phenyl-1,2-ethanediol carbonate (R-2e ) was determined by HPLC using Hewlett Packed Model HP 1100 series with a Chiralcel OD-H (eluent, hexane/isopropanol: 80:20) at rt. The retention times of R - 2e and S - 2e are 20.84 min and 23.09 min, respectively.
61. D.J. Cross, J.A. Kenny, I. Houson, L. Campbell, T. Walsgrovec, and M. Wills Tetrahedron: Asymmetry 12 2001 1801
62. 3) for (S)-1-phenyl-1,2-ethanediol carbonate}.
63. 2 yielding enantiomerically pure cyclic carbonates with complete retention of the original stereochemistry. See: X.-B. Lu, Y.-J. Zhang, K. Jun, L.-M. Luo, and H. Wang J. Catal. 227 2004 537
64. R.L. Paddock, Y. Hiyama, J.M. McKay, and S.B.T. Nguyen Tetrahedron Lett. 45 2004 2023
65. R.L. Paddock, and S.B.T. Nguyen Chem. Commun. 2004 1622
66. T. Yano, H. Matsui, T. Koike, H. Ishiguro, H. Fujihara, M. Yoshihara, and T. Maeshima Chem. Commun. 1997 1129