Rasta resin-DMAP and its use as a recyclable catalyst for the addition of carbon dioxide to epoxides

Synlett

Volumn , Issue 5, 2011, Pages 659-662

  Lu, Jinni ^a   Toy, Patrick H ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

carbon dioxide; cyclic carbonate; DMAP; polymer supported organocatalyst; polystyrene

Indexed keywords

4 DIMETHYLAMINOPYRIDINE; CARBON DIOXIDE; EPOXIDE; RESIN;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERIZATION; MORPHOLOGY; PROCESS OPTIMIZATION; SCANNING ELECTRON MICROSCOPY; SYNTHESIS; TEMPERATURE;

EID: 79952447129     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259690     Document Type: Article

References (54)

1. Lu J, Toy P H., Chem. Rev. 2009 109 815
2. Hodges J C., Harikrishnan L S., Ault-Justus S, J. Comb. Chem. 2000 2 80
3. Lindsley C W., Hodges J C., Filzen G F., Watson B M., Geyer A G., J. Comb. Chem. 2000 2 550
4. McAlpine S R., Lindsley C W., Hodges J C., Leonard D M., Filzen G F., J. Comb. Chem. 2001 3 1
5. Wisnoski D D., Leister W H., Strauss K A., Zhao Z, Lindsley C W., Tetrahedron Lett. 2003 44 4321
6. Fournier D, Pascual S, Montembault V, Haddleton D M., Fontaine L, J. Comb. Chem. 2006 8 522
7. Fournier D, Pascual S, Montembault V, Fontaine L, J. Polym. Sci., Part A: Polym. Chem. 2006 44 5316
8. Pawluczyk J M., McClain R T., Denicola C, Mulhearn J J., Rudd D J., Lindsley C W., Tetrahedron Lett. 2007 48 1497
9. Chen G, Tao L, Mantovani G, Geng J, Nystroem D, Haddleton D M., Macromolecules 2007 40 7513
10. Leung P S.-W, Teng Y, Toy P H., Synlett 2010 1997
11. Leung P S.-W, Teng Y, Toy P H., Org. Lett. 2010 12 4996
12. For our work regarding cross-linked polymers, see:, Kwok M, Choi W, He H S., Toy P H., J. Org. Chem. 2003 68 9831
13. Zhao L J., He H S., Shi M, Toy P H., J. Comb. Chem. 2004 6 680
14. Zhao L.-J, Kwong C K.-W, Shi M, Toy P H., Tetrahedron 2005 61 12026
15. For our work regarding noncross-linked polymers, see:, Harned A M., He H S., Toy P H., Flynn D L., Hanson P R., J. Am. Chem. Soc. 2005 127 52
16. He H S., Yan J J., Shen R, Zhuo S, Toy P H., Synlett 2006 563
17. Kwong C K.-W, Fu M Y., Law H C.-H, Toy P H., Synlett 2010 2617
18. Chung C W. Y., Toy P H., J. Comb. Chem. 2007 9 155
19. Kwong C K.-W, Huang R, Zhang M, Shi M, Toy P H., Chem. Eur. J. 2007 13 2369
20. For selected reviews regarding the addition of carbon dioxide to epoxides to form cyclic carbonates, see:, Dai W.-L, Luo S.-L, Yin S.-F, Au C.-T, Appl. Catal., A 2009 366 2
21. Sakakura T, Kohno K, Chem. Commun. 2009 1312
22. North M, Pasquale R, Young C, Green Chem. 2010 12 1514
23. For the organocatalytic addition of carbon dioxide to epoxides, see:, Shiels R A., Jones C W., J. Mol. Catal. A: Chem. 2007 261 160; and references cited therein
24. Qi C, Jiang H, Wang Z, Zou B, Yang S, Synlett 2007 255
25. Barkakaty B, Morino K, Sudo A, Endo T, Green Chem. 2010 12 42
26. For selected reviews regarding polymer-supported organocatalysts, see:, Benaglia M, Puglisi A, Cozzi F, Chem. Rev. 2003 103 3401
27. Benaglia M, New J. Chem. 2006 30 1525
28. Cozzi F, Adv. Synth. Catal. 2006 348 1367
29. Gruttadauria M, Giacalone F, Noto R, Chem. Soc. Rev. 2008 37 1666
30. Kristensen T E., Hansen T, Eur. J. Org. Chem. 2010 3179
31. For the use of polymer-supported organocatalysts in the addition of carbon dioxide to epoxides, see:, Xie H, Duan H, Li S, Zhang S, New J. Chem. 2005 29 1199
32. Du Y, Wang J.-Q, Chen J.-Y, Cai F, Tian J.-S, Kong D.-L, He L.-N, Tetrahedron Lett. 2006 47 1271
33. Jagtap S R., Raje V P., Samant S D., Bhanage B M., J. Mol. Catal. A: Chem. 2007 266 69
34. Qi C.-R, Jiang H.-F, Wang Z.-Y, Zou B, Chin. J. Chem. 2007 25 1051
35. Qi C, Ye J, Zeng W, Jiang H, Adv. Synth. Catal. 2010 352 1925
36. For the use of other polymers, such as ion-exchange resins, polyaniline salts, and immobilized ionic liquids, to catalyze the addition of carbon dioxide to epoxides, see:, Du Y, Cai F, Kong D.-L, He L.-N, Green Chem. 2005 7 518
37. He J, Wu T, Zhang Z, Ding K, Han B, Xie Y, Jiang T, Liu Z, Chem. Eur. J. 2007 13 6992
38. Xie Y, Zhang Z, Jiang T, He J, Han B, Wu T, Ding K, Angew. Chem. Int. Ed. 2007 46 7255
39. Toy P H., Janda K D., Tetrahedron Lett. 1999 40 6329
40. Toy P H., Reger T S., Janda K D., Aldrichimica Acta 2000 33 87
41. Toy P H., Reger T S., Garibay P, Garno J C., Malikayil J A., Liu G.-Y, Janda K D., J. Comb. Chem. 2001 3 117
42. Choi M K. W., Toy P H., Tetrahedron 2004 60 2903
43. Yue Y, Yu X.-Q, Pu L, Chem. Eur. J. 2009 15 5104
44. Bollini M, González M, Bruno A M., Tetrahedron Lett. 2009 50 1507
45. Ko K, Nakano K, Watanabe S, Ichikawa Y, Kotsuki H, Tetrahedron Lett. 2009 50 4025
46. Deb I, Shanbhag P, Mobin S M., Namboothiri I N. N., Eur. J. Org. Chem. 2009 4091
47. Mhasni O, Rezgui F, Tetrahedron Lett. 2010 51 586
48. Naidu K C., Babu G R., Gangaiah L, Mukkanti K, Madhusudhan G, Tetrahedron Lett. 2010 51 1226
49. Angelini T, Fringuelli F, Lanari D, Pizzo F, Vaccaro L, Tetrahedron Lett. 2010 51 1566
50. Goncalves S, Nicolas M, Wagner A, Baati R, Tetrahedron Lett. 2010 51 2348
51. Aoki S, Kotani S, Sugiura M, Nakajima M, Tetrahedron Lett. 2010 51 3547
52. Hudhomme P, Synlett 2010 1331
53. Vuluga D, Legros J, Crousse B, Bonnet-Delpon D, Chem. Eur. J. 2010 16 1776
54. Helou M, Miserque O, Brusson J.-M, Carpentier J.-F, Guillaume S M., Chem. Eur. J. 2010 16 13805