Rhodium-catalyzed polymerization of 3,3-diarylcyclopropenes involving a 1,4-rhodium migration

Journal of the American Chemical Society

Volumn 136, Issue 22, 2014, Pages 7849-7852

  Shintani, Ryo ^a   Iino, Ryo ^a   Nozaki, Kyoko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; POLYMERIZATION;

METAL-CATALYZED; POLYMERIZATION METHOD; POLYMERIZATION REACTION; RHODIUM-CATALYZED;

RHODIUM;

1,4 RHODIUM; 3,3 DIARYLCYCLOPROPENE DERIVATIVE; ORGANORHODIUM; POLY(CYCLOPROPYLENE PHENYLENE); PROPYLENE; RHODIUM; RHODIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; POLYMERIZATION;

EID: 84901912790     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja5032002     Document Type: Article

References (58)

1. Müller, D.; Alexakis, A. Chem. Commun. 2012, 48, 12037
2. Tian, P.; Dong, H.-Q.; Lin, G.-Q. ACS Catal. 2012, 2, 95
3. Edwards, H. J.; Hargrave, J. D.; Penrose, S. D.; Frost, C. G. Chem. Soc. Rev. 2010, 39, 2093
4. Miura, T.; Murakami, M. Chem. Commun. 2007, 217
5. Yoshida, K.; Hayashi, T. In Boronic Acids; Hall, D. G., Ed.; Wiley-VCH: Weinheim, 2005; p 171.
6. Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829
7. Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169
8. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
9. Shiotsuki, M.; Sanda, F.; Masuda, T. Polym. Chem. 2011, 2, 1044
10. Aoki, T.; Kaneko, T.; Teraguchi, M. Polymer 2006, 47, 4867
11. Mayershofer, M. G.; Nuyken, O. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 5723
12. Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464
13. Matsuda, T.; Shigeno, M.; Murakami, M. J. Am. Chem. Soc. 2007, 129, 12086
14. Seiser, T.; Roth, O. A.; Cramer, N. Angew. Chem., Int. Ed. 2009, 48, 6320
15. Shigeno, M.; Yamamoto, T.; Murakami, M. Chem.-Eur. J. 2009, 15, 12929
16. Seiser, T.; Cramer, N. Chem.-Eur. J. 2010, 16, 3383
17. Seiser, T.; Cathomen, G.; Cramer, N. Synlett 2010, 1699
18. Seiser, T.; Cramer, N. Angew. Chem., Int. Ed. 2010, 49, 10163
19. Shintani, R.; Hayashi, T. Org. Lett. 2011, 13, 350
20. Matsuda, T.; Suda, Y.; Takahashi, A. Chem. Commun. 2012, 48, 2988
21. Prakash, P.; Jijy, E.; Shimi, M.; Aparna, P. S.; Suresh, E.; Radhakrishnan, K. V. RSC Adv. 2013, 3, 19933
22. Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918
23. Miura, T.; Sasaki, T.; Nakazawa, H.; Murakami, M. J. Am. Chem. Soc. 2005, 127, 1390
24. Shintani, R.; Okamoto, K.; Hayashi, T. J. Am. Chem. Soc. 2005, 127, 2872
25. Yamabe, H.; Mizuno, A.; Kusama, H.; Iwasawa, N. J. Am. Chem. Soc. 2005, 127, 3248
26. Shintani, R.; Hayashi, T. Org. Lett. 2005, 7, 2071
27. Shintani, R.; Isobe, S.; Takeda, M.; Hayashi, T. Angew. Chem., Int. Ed. 2010, 49, 3795
28. Sasaki, K.; Nishimura, T.; Shintani, R.; Kantchev, E. A. B.; Hayashi, T. Chem. Sci. 2012, 3, 1278
29. Ma, S.; Gu, Z. Angew. Chem., Int. Ed. 2005, 44, 7512
30. Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077
31. Schleyer, P. v. R.; Williams, J. E.; Blanchard, K. R. J. Am. Chem. Soc. 1970, 92, 2377
32. Wiberg, K. B.; Bartley, W. J. J. Am. Chem. Soc. 1960, 82, 6375
33. Rush, S.; Reinmuth, A.; Risse, W.; O'Brien, J.; Ferro, D. R.; Tritto, I. J. Am. Chem. Soc. 1996, 118, 12230
34. Rush, S.; Reinmuth, A.; Risse, W. Macromolecules 1997, 30, 7375
35. Singh, R.; Czekelius, C.; Schrock, R. R. Macromolecules 2006, 39, 1316
36. Binder, W. H.; Kurzhals, S.; Pulamagatta, B.; Decker, U.; Pawar, G. M.; Wang, D.; Kühnel, C.; Buchmeriser, M. R. Macromolecules 2008, 41, 8405
37. Copolymerization of cyclopropenes with ethylene or 1-alkenes has also been described: Andreades, S.; Baird, R. L. US 3,919,227 A 19751111, 1975.
38. A rhodium-catalyzed reaction of 3,3-diarylcyclopropenes involving a 1,4-rhodium migration was reported: Nishimoto, S.; Sawano, T.; Nishimura, T.; Hayashi, T. Abstracts of Papers, 93rd Annual Meeting of the Chemical Society of Japan, Shiga; Chemical Society of Japan: Tokyo, 2013; 4F5-03.
39. Ueura, K.; Miyamura, S.; Satoh, T.; Miura, M. J. Organomet. Chem. 2006, 691, 2821
40. Shintani, R.; Tsutsumi, Y.; Nagaosa, M.; Nishimura, T.; Hayashi, T. J. Am. Chem. Soc. 2009, 131, 13588
41. Shintani, R.; Takeda, M.; Tsuji, T.; Hayashi, T. J. Am. Chem. Soc. 2010, 132, 13168
42. Ueda, M.; Miyaura, N. J. Organomet. Chem. 2000, 595, 31
43. Miura, T.; Sasaki, T.; Nakazawa, H.; Murakami, M. J. Am. Chem. Soc. 2005, 127, 1390
44. Tabata, M.; Yang, W.; Yokota, K. Polym. J. 1990, 22, 1105
45. Yang, W.; Tabata, M.; Kobayashi, S.; Yokota, K.; Shimizu, A. Polym. J. 1991, 23, 1135
46. Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009
47. Tabata, M.; Yang, W.; Yokota, K. J. Polym. Sci., Part A: Polym. Chem. 1994, 32, 1113
48. Tabata, M.; Yokota, K.; Namioka, M. Macromol. Chem. Phys. 1995, 196, 2969
49. Aramata, K.; Kajiwara, A.; Kamachi, M. Macromolecules 1995, 28, 4774
50. Kishimoto, Y.; Itou, M.; Miyatake, T.; Ikariya, T.; Noyori, R. Macromolecules 1995, 28, 6662
51. Itooka, R.; Iguchi, Y.; Miyaura, N. J. Org. Chem. 2003, 68, 6000
52. Shintani, R.; Okamoto, K.; Otomaru, Y.; Ueyama, K.; Hayashi, T. J. Am. Chem. Soc. 2005, 127, 54
53. Miura, T.; Shimada, M.; Murakami, M. J. Am. Chem. Soc. 2005, 127, 1094
54. Kina, A.; Yasuhara, Y.; Nishimura, T.; Iwamura, H.; Hayashi, T. Chem.-Asian J. 2006, 1, 707
55. Kurahashi, T.; Shinokubo, H.; Osuka, A. Angew. Chem., Int. Ed. 2006, 45, 6336
56. Chen, Y.; Lee, C. J. Am. Chem. Soc. 2006, 128, 15598
57. Miura, T.; Ueda, K.; Takahashi, Y.; Murakami, M. Chem. Commun. 2008, 5366
58. Artok, L.; Kus, M.; Ürer, B. N.; Türkmen, G.; Aksin-Artok, Ö. Org. Biomol. Chem. 2010, 8, 2060