Synthesis of [8]cycloparaphenylene from a square-shaped tetranuclear platinum complex

Angewandte Chemie - International Edition

Volumn 49, Issue 4, 2010, Pages 757-759

  Yamago, Shigeru ^a   Watanabe, Yoshiki ^a   Iwamoto, Takahiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Conjugation; Cyclophanes; Nanotubes; Platinum; Polycycles

Indexed keywords

CHEMICAL EQUATIONS; CONJUGATION; CYCLOPHANES; HIGH YIELD; POLYCYCLES; REACTION CONDITIONS; SELECTIVE SYNTHESIS; TETRANUCLEAR PLATINUM COMPLEX;

COMPLEXATION; NANOTUBES; PLATINUM; REACTION INTERMEDIATES; SYNTHESIS (CHEMICAL);

PLATINUM COMPOUNDS;

EID: 74849115028     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200905659     Document Type: Article

References (41)

1. a) A. Schröder, H.-B. Mekelburger, F. Vögtle, Top. Curr. Chem. 1994, 172, 179;
2. b) T. Kawase, H. Kurata, Chem. Rev. 2006, 706, 5250;
3. c) K. Tahara, Y. Tobe, Chem. Rev. 2006, 706, 5274;
4. d) L. T. Scott, Angew. Chem. 2003, 175, 4265;
5. Angew. Chem Int. Ed. 2003, 42, 4133.
6. The synthesis of hoop-shaped (formal) π-conjugated macrocycles has been reported: a) R. L. Viavattene, F. D. Greene, L. D. Cheung, R. Majeste, L. M. Trefonas, J. Am. Chem. Soc. 1974, 96, 4342;
7. b) S. Kammermeier, R. Herges, Angew. Chem. 1996, 108, 470;
8. Angew. Chem. Int. Ed. Engl. 1996, 35, 417;
9. c) S. Kammermeier, P. G. Jones, R. Herges, Angew. Chem. 1996, 108, 2834;
10. Angew. Chem. Int. Ed. Engl. 1996, 35, 2669;
11. d) S. Kammermeier, P. G. Jones, R. Herges, Angew. Chem. 1997, 109, 2317;
12. Angew. Chem. Int. Ed. Engl. 1997, 36, 2200;
13. e) T. Kawase, H. R. Darabi, M. Oda, Angew. Chem. 1996, 708,2803;
14. Angew. Chem. Int. Ed. Engl. 1996, 35, 2664;
15. f) M. Ohkita, K. Ando, T. Tsuji, Chem. Commun. 2001,2570;
16. g) E. Nakamura, K. Tahara, Y. Matsuo, M. Sawamura, J. Am. Chem. Soc. 2003, 125, 2834.
17. a) B. D. Steinberg, L. T. Scott, Angew. Chem. 2009, 121, 5504;
18. Angew. Chem. Int. Ed. 2009, 48, 5400;
19. b)R. Friederich, M. Nieger, F. Vögtle, Chem. Ber. 1993,126,1723.
20. R. Jasti, J. Bhattacharjee, J. B. Neaton, C. R. Bertozzi, J. Am. Chem. Soc 2008, 130,17646.
21. H. Takaba, H. Omachi, Y. Yamamoto, J. Bouffard, K. Itami, Angew. Chem. 2009, 121, 6228;
22. Angew. Chem. Int. Ed 2009, 48, 6112.
23. Our previous interests in. hoop-shaped π-conjugated molecules: a) E. Nakamura, S. Yamago, Acc. Chem. Res. 2002, 35, 867;
24. b) E. Nakamura, H. Tokuyama, S. Yamago, T. Shiraki, Y. Sugiura, Bull. Chem. Soc. Jpn. 1996, 69, 2143.
25. a) M. Fujita, J. Yazaki, K. Ogura, J. Am. Chem. Soc. 1990, 772, 5645;
26. b) M. Fujita, J. Yazaki, K. Ogura, J. Chem. Lett. 1991, 1031;
27. c)P.J. Stang, D.H. Cao, J. Am. Chem. Soc. 1994, 116, 4981;
28. d) D. C. Caskey, R. K. Shoemaker, J. Michl, Org. Lett. 2004, 6, 2093.
29. a) M. Fujita, M. Tominaga, A. Hori, B. Therrien, Acc. Chem. Res. 2005, 38, 369;
30. b) S. Leininger, B. Olenyuk, P. J. Stang, Chem. Rev. 2000, 100, 853.
31. A square shaped tetranuclear platinum-butadiyne complex has been reported. S. M. ALQaisi, K. J. Galat, M. Chai, D. G. Ray, III, P. L. Rinaldi, C. A. Tessier, W. J. Youngs, J. Am. Chem. Soc. 1998, 120, 12149.
32. The random synthesis of [njcyclothiophenes mediated by oligometallic platinum complexes has been reported:B a) G. Fuhrmann, T. Debaerdemaeker, P. Bäuerle, Chem. Commun. 2003, 948;
33. b) F. Zhang, G. Götz, H. D. F. Winkler, C. A. Schalley, P. Bäuerle, Angew. Chem. 2009, 121, 6758;
34. Angew. Chem. Int. Ed. 2009, 48, 6632.
35. n] and hydrogen by the DFT calculation. No zeropoint energy correlation was included. Our calculated values are very close to those obtained by Itami and co-workers (reference [5]) but considerably different from those reported by Bertozzi and co-workers (see reference [4]).
36. M. D. Curtis, A. L. Allred, J. Am. Chem. Soc. 1965, 87, 2554.
37. C. Eaborn, K. J. Odell, A. Pidcock, J. Chem. Soc Dalton 1978, 357.
38. A. Yahav-Levi, I. Goldberg, A. Vigalok, J. Am. Chem. Soc. 2006, 128, 8710.
39. A. Yahav-Levi, I. Goldberg, A. Vigalok, A. N. Vedemikov, J. Am. Chem. Soc. 2008, 130, 724.
40. S. Shekhar, J. F. Hartwig, J. Am. Chem. Soc. 2004, 126, 13016.
41. We could not observe a melting point below 300°C.