Bifunctional catalysts based on m-phenylene-bridged porphyrin dimer and trimer platforms: Synthesis of cyclic carbonates from carbon dioxide and epoxides

Angewandte Chemie - International Edition

Volumn 54, Issue 1, 2015, Pages 134-138

  Maeda, Chihiro ^a   Taniguchi, Tomoya ^a   Ogawa, Kanae ^a   Ema, Tadashi ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Carbon dioxide fixation; Cyclic carbonates; Homogeneous catalysis; Porphyrinoids; Zinc

Indexed keywords

CARBON; CARBON DIOXIDE; CARBONATES; CATALYSTS; CHEMICAL COMPOUNDS; DIMERS; LOADING; PORPHYRINS; REACTION KINETICS; SYNTHESIS (CHEMICAL); ZINC; ZINC COMPOUNDS;

BI-FUNCTIONAL CATALYSTS; CARBON DIOXIDE FIXATION; CYCLIC CARBONATES; HOMOGENEOUS CATALYSIS; MAGNESIUM CATALYSTS; PORPHYRINOIDS; STILLE COUPLING REACTION; SYNTHESIS OF CYCLIC CARBONATES;

CATALYST ACTIVITY;

EID: 84920163168     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201409729     Document Type: Article

References (69)

1. T. Sakakura, J.-C. Choi, H. Yasuda, Chem. Rev. 2007, 107, 2365
2. D. J. Darensbourg, Chem. Rev. 2007, 107, 2388
3. T. Sakakura, K. Kohno, Chem. Commun. 2009, 1312
4. M. North, R. Pasquale, C. Young, Green Chem. 2010, 12, 1514
5. S. N. Riduan, Y. Zhang, Dalton Trans. 2010, 39, 3347
6. S. Klaus, M.W. Lehenmeier, C. E. Anderson, B. Rieger, Coord. Chem. Rev. 2011, 255, 1460
7. M. Cokoja, C. Bruckmeier, B. Rieger, W. A. Herrmann, F. E. Kühn, Angew. Chem. Int. Ed. 2011, 50, 8510
8. M.Cokoja, C.Bruckmeier, B.Rieger, W. A.Herrmann, F. E.Kühn, Angew. Chem. 2011, 123, 8662
9. Y. Tsuji, T. Fujihara, Chem. Commun. 2012, 48, 9956
10. D. J. Darensbourg, S. J. Wilson, Green Chem. 2012, 14, 2665
11. N. Kielland, C. J. Whiteoak, A.W. Kleij, Adv. Synth. Catal. 2013, 355, 2115
12. C. Maeda, Y. Miyazaki, T. Ema, Catal. Sci. Technol. 2014, 4, 1482.
13. Various transformations of CO2 : S. N. Riduan, Y. Zhang, J. Y. Ying, Angew. Chem. Int. Ed. 2009, 48, 3322;
14. Angew. Chem. 2009, 121, 3372
15. Y. Kayaki, M. Yamamoto, T. Ikariya, Angew. Chem. Int. Ed. 2009, 48, 4194
16. Angew. Chem. 2009, 121, 4258
17. W.-Z. Zhang,W.-J. Li, X. Zhang, H. Zhou, X.-B. Lu, Org. Lett. 2010, 12, 4748
18. L. Gu, Y. Zhang, J. Am. Chem. Soc. 2010, 132, 914
19. A. Berkefeld, W. E. Piers, M. Parvez, J. Am. Chem. Soc. 2010, 132, 10660
20. H. Mizuno, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2011, 133, 1251
21. H. Ohmiya, M. Tanabe, M. Sawamura, Org. Lett. 2011, 13, 1086
22. T. Fujihara, K. Nogi, T. Xu, J. Terao, Y. Tsuji, J. Am. Chem. Soc. 2012, 134, 9106
23. M. L. Lejkowski, R. Lindner, T. Kageyama, G. É. Bódizs, P. N. Plessow, I. B. Müller, A. Schäfer, F. Rominger, P. Hofmann, C. Futter, S. A. Schunk, M. Limbach, Chem. Eur. J. 2012, 18, 14017
24. N. Ishida, Y. Shimamoto, M. Murakami, Angew. Chem. Int. Ed. 2012, 51, 11750
25. Angew. Chem. 2012, 124, 11920
26. T. Le-n, A. Correa, R. Martin, J. Am. Chem. Soc. 2013, 135, 1221
27. T. Ishida, S. Kikuchi, T. Yamada, Org. Lett. 2013, 15, 3710
28. B. Yu, H. Zhang, Y. Zhao, S. Chen, J. Xu, C. Huang, Z. Liu, Green Chem. 2013, 15, 95
29. A. Ueno, Y. Kayaki, T. Ikariya, Green Chem. 2013, 15, 425
30. A. Correa, T. León, R. Martin, J. Am. Chem. Soc. 2014, 136, 1062
31. Y. Makida, E. Marelli, A. M. Z. Slawin, S. P. Nolan, Chem. Commun. 2014, 50, 8010
32. W.-J. Yoo, T. V. Q. Nguyen, S. Kobayashi, Angew. Chem. Int. Ed. 2014, 53, 10213
33. Angew. Chem. 2014, 126, 10377.
34. Recent examples of metal complexes: W. Clegg, R. W. Harrington, M. North, R. Pasquale, Chem. Eur. J. 2010, 16, 6828
35. A. Decortes,M. M. Belmonte, J. Benet-Buchholz, A.W. Kleij, Chem. Commun. 2010, 46, 4580
36. C. J. Whiteoak, N. Kielland, V. Laserna, E. C. Escudero-Adán, E. Martin, A.W. Kleij, J. Am. Chem. Soc. 2013, 135, 1228
37. M. V. Escárcega-Bobadilla, M. M. Belmonte, E. Martin, E. C. Escudero-Adán, A.W. Kleij, Chem. Eur. J. 2013, 19, 2641
38. H. V. Babu, K. Muralidharan, Dalton Trans. 2013, 42, 1238
39. S. H. Kim, D. Ahn, M. J. Go, M. H. Park, M. Kim, J. Lee, Y. Kim, Organometallics 2014, 33, 2770.
40. Examples of metalloporphyrins: T. Aida, S. Inoue, J. Am. Chem. Soc. 1983, 105, 1304
41. W. J. Kruper, D. V. Dellar, J. Org. Chem. 1995, 60, 725
42. R. L. Paddock, Y. Hiyama, J. M. Mckay, S. T. Nguyen, Tetrahedron Lett. 2004, 45, 2023
43. L. Jin, H. Jing, T. Chang, X. Bu, L.Wang, Z. Liu, J. Mol. Catal. A 2007, 261, 262
44. F. Ahmadi, S. Tangestaninejad, M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork, A. R. Khosropour, Inorg. Chem. Commun. 2011, 14, 1489.
45. Recent examples of organocatalysts: H. Zhou, Y.-M. Wang, W.-Z. Zhang, J.-P. Qu, X.-B. Lu, Green Chem. 2011, 13, 644
46. S. Liang, H. Liu, T. Jiang, J. Song, G. Yang, B. Han, Chem. Commun. 2011, 47, 2131
47. L. Han, H.-J. Choi, S.-J. Choi, B. Liu, D.-W. Park, Green Chem. 2011, 13, 1023
48. N. Aoyagi, Y. Furusho, T. Endo, Chem. Lett. 2012, 41, 240
49. Z.-Z. Yang, Y.-N. Zhao, L.-N. He, J. Gao, Z.-S. Yin, Green Chem. 2012, 14, 519
50. B. Chatelet, L. Joucla, J.-P. Dutasta, A. Martinez, K. C. Szeto, V. Dufaud, J. Am. Chem. Soc. 2013, 135, 5348
51. Y.-B.Wang, D.-S. Sun, H. Zhou, W.-Z. Zhang, X.-B. Lu, Green Chem. 2014, 16, 2266.
52. Polycarbonate synthesis from epoxide and CO2 : K. Nakano, S. Hashimoto, K. Nozaki, Chem. Sci. 2010, 1, 369
53. S. Klaus, M.W. Lehenmeier, E. Herdtweck, P. Deglmann, A. K. Ott, B. Rieger, J. Am. Chem. Soc. 2011, 133, 13151
54. G.-P. Wu, S.-H. Wei, W.-M. Ren, X.-B. Lu, T.-Q. Xu, D. J. Darensbourg, J. Am. Chem. Soc. 2011, 133, 15191
55. J. G. Kim, C. D. Cowman, A. M. LaPointe, U. Wiesner, G.W. Coates, Macromolecules 2011, 44, 1110
56. K. Nakano, K. Kobayashi, T. Ohkawara, H. Imoto, K. Nozaki, J. Am. Chem. Soc. 2013, 135, 8456
57. P. K. Saini, C. Romain, C. K. Williams, Chem. Commun. 2014, 50, 4164
58. W. C. Ellis, Y. Jung, M. Mulzer, R. D. Girolamo, E. B. Lobkovsky, G. W. Coates, Chem. Sci. 2014, 5, 4004.
59. T. Ema, Y. Miyazaki, S. Koyama, Y. Yano, T. Sakai, Chem. Commun. 2012, 48, 4489
60. T. Ema, Y. Miyazaki, T. Taniguchi, J. Takada, Green Chem. 2013, 15, 2485
61. T. Ema, Y. Miyazaki, J. Shimonishi, C. Maeda, J. Hasegawa, J. Am. Chem. Soc. 2014, DOI: 10.1021/ja507665a.
62. B. List, Acc. Chem. Res. 2004, 37, 548
63. W. Notz, F. Tanaka, C. F. Barbas III, Acc. Chem. Res. 2004, 37, 580
64. S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471.
65. nd ed., Garland, New York, 1999.
66. A. Wiehe, Y. M. Shaker, J. C. Brandt, S. Mebs, M. O. Senge, Tetrahedron 2005, 61, 5535.
67. Initially, we tried to synthesize triporphyrin by the Suzuki-Miyaura coupling reaction of 7 with benzene-1,3,5-triboronic acid pinacol ester. However, little or no product was obtained.
68. nd ed., Freeman, New York, 1985
69. R. Wolfenden, M. J. Snider, Acc. Chem. Res. 2001, 34, 938.