[3]Rotaxane-based dinuclear palladium catalysts for ring-closure Mizoroki-Heck reaction

Organic Letters

Volumn 13, Issue 15, 2011, Pages 3774-3777

  Suzaki, Yuji ^a   Shimada, Kyoichi ^a   Chihara, Eriko ^a   Saito, Takashi ^a   Tsuchido, Yoshitaka ^a   Osakada, Kohtaro ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79961049724     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201357b     Document Type: Article

References (47)

1. Sauvage, J.-P.; Dietrich-Buchecker, C. In Molecular Catenanes, Rotaxanes and Knots; Wiley-VCH: Weinheim, 1999.
2. Jäger, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 930
3. Nepogodiev, S. A.; Stoddart, J. F. Chem. Rev. 1998, 98, 1959
4. Hubin, T. J.; Busch, D. H. Coord. Chem. Rev. 2000, 200-202, 5
5. Huang, F.; Gibson, H. W. Prog. Polym. Sci. 2005, 30, 982
6. Lehn, J.-M. Chem. Soc. Rev. 2007, 36, 151
7. Stoddart, J. F. Chem. Soc. Rev. 2009, 38, 1802
8. De Greef, T. F. A.; Smulders, M. M. J.; Wolffs, M.; Schenning, A. P. H. J.; Sijbesma, R. P.; Meijer, E. W. Chem. Rev. 2009, 109, 5687
9. Harada, A.; Hashidzume, A.; Yamaguchi, H.; Takashima, Y. Chem. Rev. 2009, 109, 5974
10. Niu, Z.; Gibson, H. W. Chem. Rev. 2009, 109, 6024
11. Fang, L.; Olson, M. A.; Benítez, D.; Tkatchouk, E.; Goddard, W. A., III; Stoddart, J. F. Chem. Soc. Rev. 2010, 39, 17
12. Durola, F.; Sauvage, J.-P.; Wenger, O. S. Coord. Chem. Rev. 2010, 254, 1748
13. Hänni, K. D.; Leigh, D. A. Chem. Soc. Rev. 2010, 39, 1240
14. Osakada, K.; Sakano, T.; Horie, M.; Suzaki, Y. Coord. Chem. Rev. 2006, 250, 1012
15. Suzaki, Y.; Taira, T.; Osakada, K.; Horie, M. Dalton Trans. 2008, 4823
16. Suzaki, Y.; Taira, T.; Osakada, K. J. Mater. Chem. 2011, 21, 931
17. Bissell, R. A.; Córdova, E.; Kaifer, A. E.; Stoddart, J. F. Nature 1994, 369, 133
18. Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2000, 39, 3348
19. Special issue on molecular machines: Acc. Chem. Res. 2001, 34, 409.
20. Collier, C. P.; Wong, E. W.; Belohradský, M.; Raymo, F. M.; Stoddart, J. F.; Kuekes, P. J.; Williams, R. S.; Heath, J. R. Science 1999, 285, 391
21. Berná, J.; Leigh, D. A.; Lubomska, M.; Mendoza, S. M.; Pérez, E. M.; Rudolf, P.; Teobaldi, G.; Zerbetto, F. Nature Mater. 2005, 4, 704
22. Okumura, Y.; Ito, K. Adv. Mater. 2001, 13, 485
23. Oku, T.; Furusho, Y.; Takata, T. Angew. Chem., Int. Ed. 2004, 43, 966
24. Thordarson, P.; Bijsterveld, E. J. A.; Rowan, A. E.; Nolte, R. J. M. Nature 2003, 424, 915
25. Tachibana, Y.; Kihara, N.; Takata, T. J. Am. Chem. Soc. 2004, 126, 3438
26. Hattori, G.; Hori, T.; Miyake, Y.; Nishibayashi, Y. J. Am. Chem. Soc. 2007, 129, 12930
27. Sato, T.; Takata, T. Polymer J. 2009, 41, 470
28. Cantrill, S. J.; Grubbs, R. H.; Lanari, D.; Leung, K. C.-F.; Nelson, A.; Poulin-Kerstien, K. G.; Smidt, S. P.; Stoddart, J. F.; Tirrell, D. A. Org. Lett. 2005, 7, 4213
29. Parham, A. H.; Windisch, B.; Vögtle, F. Eur. J. Org. Chem. 1999, 1233
30. Hu, Y.-Z.; Chamchoumis, C.; Grebowicz, J. S.; Thummel, R. P. Inorg. Chem. 2002, 41, 2296
31. Mori, A.; Mohamed Ahmed, M. S.; Sekiguchi, A.; Masui, K.; Koike, T. Chem. Lett. 2002, 756
32. Mohamed Ahmed, M. S.; Sekiguchi, A.; Masui, K.; Mori, A. Bull. Chem. Soc. Jpn. 2005, 78, 160
33. Bosch, E.; Barnes, C. L. Inorg. Chem. 2001, 40, 3097
34. Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18
35. Coumans, R. G. E.; Elemans, J. A. A. W.; Thordarson, P.; Nolte, R. J. M.; Rowan, A. E. Angew. Chem., Int. Ed. 2003, 42, 650
36. Hannam, J. S.; Kidd, T. J.; Leigh, D. A.; Wilson, A. J. Org. Lett. 2003, 5, 1907
37. Suzaki, Y.; Osakada, K. Chem. Lett. 2006, 35, 374
38. Suzaki, Y.; Osakada, K. Dalton Trans. 2007, 2376
39. Suzaki, Y.; Chihara, E.; Takagi, A.; Osakada, K. Dalton Trans. 2009, 9881
40. Ashton, P. R.; Campbell, P. J.; Chrystal, E. J. T.; Glink, P. T.; Menzer, S.; Philp, D.; Spencer, N.; Stoddart, J. F.; Tasker, P. A.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1865
41. Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360
42. Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581
43. Heck, R. F.; Nolley, J. P., Jr. J. Org. Chem. 1972, 37, 2320
44. Oestreich, M. The Mizoroki-Heck Reaction; Wiley: Weinheim, 2009.
45. Mizoroki-Heck reaction of aryl halides and tert -butyl acrylate catalyzed by dichloro{bis(pyridylethynylbenzene)}palladium(II) complex: Kawano, T.; Shinomaru, T.; Ueda, I. Org. Lett. 2002, 4, 2545
46. Polycondensation polymerization of 8 and divinylbenzene by Mizoroki-Heck reaction: Suzuki, M.; Lim, J.-C.; Saegusa, T. Macromolecules 1990, 23, 1574
47. 2 (runs 2 and 4). Thus, comparison of the product yields did not provide useful information on the reaction details in this case.