Rhenium-catalyzed synthesis of 3-imino-1-isoindolinones by C-H bond activation: Application to the synthesis of polyimide derivatives

Angewandte Chemie - International Edition

Volumn 52, Issue 45, 2013, Pages 11879-11883

  Sueki, Shunsuke ^a,b   Guo, Yuanfang ^a   Kanai, Motomu ^a   Kuninobu, Yoichiro ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

C H activation; isocyanate; polymers; rhenium; synthetic methods

Indexed keywords

C-H ACTIVATION; CH-BOND ACTIVATION; GRAM SCALE; HIGH YIELD; IMIDATES; ISOCYANATE; SYNTHETIC METHODS; TITLE COMPOUNDS;

ACTIVATION ANALYSIS; CATALYSIS; POLYIMIDES; POLYMERS; RHENIUM;

RHENIUM COMPOUNDS;

IMIDE; ISOCYANATE; ISOCYANIC ACID DERIVATIVE; POLYMER; RHENIUM;

ARTICLE; C H ACTIVATION; CATALYSIS; CHEMISTRY; HYDROGEN BOND; SYNTHETIC METHODS;

C H ACTIVATION; ISOCYANATE; POLYMERS; RHENIUM; SYNTHETIC METHODS;

CATALYSIS; HYDROGEN BONDING; IMIDES; ISOCYANATES; POLYMERS; RHENIUM;

EID: 84886779743     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201306360     Document Type: Article

References (50)

1. D. A. Russell, J. W. Connell, L. B. Fogdall, J. Spacecr. Rockets 2002, 39, 833
2. J. A. Dever, S. K. Miller, E. A. Sechkar, T. N. Wittberg, High Perform. Polym. 2008, 20, 371.
3. M. Nishikawa, Y. Reznikov, J. L. West, Liq. Cryst. 1999, 26, 575
4. Q.-D. Ling, F.-C. Chang, Y. Song, C.-X. Zhu, D.-J. Liaw, D. S.-H. Chan, E.-T. Kang, K.-G. Neoh, J. Am. Chem. Soc. 2006, 128, 8732
5. N.-H. You, Y. Suzuki, D. Yorifuji, S. Ando, M. Ueda, Macromolecules 2008, 41, 6361.
6. W. Volksen, Adv. Polym. Sci. 1994, 117, 111.
7. H. Guo, M. A. Tapsak, W. P. Weber, Macromolecules 1995, 28, 4714
8. H. Guo, G. Wang, M. A. Tapsak, W. P. Weber, Macromolecules 1995, 28, 5686
9. P. Lu, J. K. Paulasari, W. P. Weber, Macromolecules 1996, 29, 8583
10. G. Wang, H. Guo, W. P. Weber, J. Organomet. Chem. 1996, 521, 351.
11. N. Masuda, S. Tanba, A. Sugie, D. Monguchi, N. Koumura, K. Hara, A. Mori, Org. Lett. 2009, 11, 2297
12. Q. Wang, R. Takita, Y. Kikuzaki, F. Ozawa, J. Am. Chem. Soc. 2010, 132, 11420
13. S. Tamba, S. Tanaka, Y. Okubo, H. Meguro, S. Okamoto, A. Mori, Chem. Lett. 2011, 40, 398.
14. Y. Kuninobu, A. Kawata, K. Takai, J. Am. Chem. Soc. 2005, 127, 13498
15. Y. Kuninobu, Y. Tokunaga, A. Kawata, K. Takai, J. Am. Chem. Soc. 2006, 128, 202
16. Y. Kuninobu, Y. Nishina, M. Shouho, K. Takai, Angew. Chem. 2006, 118, 2832
17. Angew. Chem. Int. Ed. 2006, 45, 2766
18. Y. Kuninobu, Y. Nishina, C. Nakagawa, K. Takai, J. Am. Chem. Soc. 2006, 128, 12376
19. Y. Kuninobu, Y. Nishina, T. Matsuki, K. Takai, J. Am. Chem. Soc. 2008, 130, 14062
20. Y. Kuninobu, P. Yu, K. Takai, Org. Lett. 2010, 12, 4274.
21. S. Murahashi, J. Am. Chem. Soc. 1955, 77, 6403
22. Y.-B. Zhao, B. Mariampillai, D. A. Candito, B. Laleu, M. Li, M. Lautens, Angew. Chem. 2009, 121, 1881
23. Angew. Chem. Int. Ed. 2009, 48, 1849
24. Z.-M. Sun, S.-P. Chen, P. Zhao, Chem. Eur. J. 2010, 16, 2619
25. D. N. Tran, N. Cramer, Angew. Chem. 2010, 122, 8357
26. Angew. Chem. Int. Ed. 2010, 49, 8181
27. F. W. Patureau, T. Besset, N. Kuhl, F. Glorius, J. Am. Chem. Soc. 2011, 133, 2154
28. K. Muralirajan, K. Parthasarathy, C.-H. Cheng, Angew. Chem. 2011, 123, 4255
29. Angew. Chem. Int. Ed. 2011, 50, 4169
30. D. N. Tran, N. Cramer, Angew. Chem. 2011, 123, 11294
31. Angew. Chem. Int. Ed. 2011, 50, 11098
32. R. K. Chinnagolla, M. Jeganmohan, Eur. J. Org. Chem. 2012, 417
33. B.-J. Li, H.-Y. Wang, Q.-L. Zhu, Z.-J. Shi, Angew. Chem. 2012, 124, 4014
34. Angew. Chem. Int. Ed. 2012, 51, 3948
35. P. Zhao, F. Wang, K. Han, X. Li, Org. Lett. 2012, 14, 5506
36. Y. Lian, T. Huber, K. D. Hesp, R. G. Bergman, J. A. Ellman, Angew. Chem. 2013, 125, 657
37. Angew. Chem. Int. Ed. 2013, 52, 629
38. J. Zhang, A. Ugrinov, P. Zhao, Angew. Chem. 2013, 125, 6813
39. Angew. Chem. Int. Ed. 2013, 52, 6681.
40. S. Nan'ya, T. Tange, E. Maekawa, J. Heterocycl. Chem. 1985, 22, 449
41. H. Takeuchi, S. Eguchi, J. Chem. Soc. Perkin Trans. 1 1988, 2149
42. S. Scherbakow, J. C. Namyslo, M. Gjikaj, A. Schmidt, Synlett 2009, 1964
43. J. Wang, Z. He, X. Chen, W. Song, P. Lu, Y. Wang, Tetrahedron 2010, 66, 1208
44. T. Miura, Y. Nishida, M. Morimoto, M. Yamauchi, M. Murakami, Org. Lett. 2011, 13, 1429
45. B. Liu, Y. Li, H. Jiang, M. Yin, H. Huang, Adv. Synth. Catal. 2012, 354, 2288.
46. Y. Kuninobu, Y. Tokunaga, K. Takai, Chem. Lett. 2007, 36, 872
47. K. D. Hesp, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2011, 133, 11430
48. K. Muralirajan, K. Parthasarathy, C.-H. Cheng, Org. Lett. 2012, 14, 4262
49. B. Zhou, W. Hou, Y. Yang, Y. Li, Chem. Eur. J. 2013, 19, 4701. See also: ref.-[6b].
50. C. E. Sroog, J. Polym. Sci. Part D 1976, 11, 161.