Rhodium-catalyzed activation and functionalization of the C-C bond of biphenylene

Organometallics

Volumn 20, Issue 26, 2001, Pages 5745-5750

  Iverson, Carl N ^a   Jones, William D ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIPHEHYLENE; FUCTIONALIZATION; ISONITRILE; LEWIS BASES; MIGRATION YIELD; OLEFINIC SUBSTRATES;

CARBON MONOXIDE; CATALYSIS; CHELATION; CHEMICAL ACTIVATION; CHEMICAL BONDS; COMPOSITION EFFECTS; NITROGEN COMPOUNDS; OLEFINS; PHENOLS; SUBSTITUTION REACTIONS; THERMAL EFFECTS;

RHODIUM COMPOUNDS;

EID: 0035945454     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0107946     Document Type: Article

References (46)

1. Recent reviews highlight C-C bond activation: (a) Murakami, M.; Ito, Y. in Topics in Organometallic Chemistry; Murai, S., Ed.; Springer-Verlag: New York, 1999; Vol. 3, pp 96-129.
2. (b) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 871.
3. Lin, M.; Hogan, T. E.; Sen, A. J. Am. Chem. Soc. 1996, 118, 4574.
4. Jun, C.-H.; Lee, D.-Y.; Kim, Y.-H.; Lee, H. Organometallics 2001, 20, 2929.
5. Liou, S.-Y.; van der Boom, M. E.; Milstein, D. Chem. Commun. 1998, 687,
6. Murakami, M.; Amii, H.; Shigeto, K.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 8285.
7. Beck, C. M.; Rathmill, S. E.; Park, Y. J.; Chen, J.; Crabtree, R. H.; Liable-Sands, L. M.; Rheingold, A. L. Organometallics 1999, 18, 5311.
8. Edelbach, B. L.; Lachicotte, R. J.; Jones, W. D. J. Am. Chem. Soc. 1998, 120, 2843.
9. (a) Cassar, L.; Halpern, J. J. Chem. Soc., Chem. Commun. 1970, 1082.
10. (b) Cassar, L.; Eaton, P. E.; Halpern, J. J. Am. Chem. Soc. 1970, 92, 3515.
11. (c) Song, L.; Arif, A. M.; Stang, P. J. Organometallics 1990, 9, 2792.
12. (a) Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 7346.
13. (b) Perthuisot, C.; Jones, W. D. J. Am. Chem. Soc. 1994, 116, 3647.
14. (a) Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Jones, W. D. Organometallics 1997, 16, 2016.
15. (b) Suggs, J. W.; Jun, C. H. J. Am. Chem. Soc. 1986, 108, 4679.
16. (c) Jun, C. H.; Kang, J. B.; Lim, Y. G. Tetrahedron Lett. 1995, 36, 277.
17. (d) Murakami, M.; Tsuruta, T.; Ito, Y. Angew. Chem., Int. Ed. 2000, 39, 2484.
18. (a) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Science 1993, 364, 699.
19. (b) Rybtchinski, B.; Vigalok, A.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 1996, 118, 12406.
20. (c) van der Boom, M. E.; Liou, S. Y.; Ben-David, Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 13415.
21. (d) Cohen, R.; van der Boom, M. E.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2000, 122, 7723.
22. (a) Mueller, E.; Segnittz, A. Liebigs Ann. Chem. 1973, 1538.
23. (b) Liebeskind, L. S.; Baysdon, S. L.; South, M. S.; Iyer, S.; Leeds, J. P. Tetrahedron 1985, 41, 5839.
24. (c) Huffman, M. A.; Liebeskind, L. S.; Pennington, W. T. Organometallics 1992, 11, 255.
25. (d) Murakami, M.; Amii, H.; Ito, Y. Nature 1994, 370, 540.
26. (e) Murakami, M.; Amii, H.; Shigeto, K.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 8285.
27. (f) Murakami, M.; Itahashi, T.; Amii, H.; Takahashi, K.; Ito, Y. J. Am. Chem. Soc. 1998, 120, 9949.
28. (g) Murakami, M.; Takahashi, K.; Amii, H.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 9307.
29. 2, has recently been reported to facilitate the reversible C-C bond activation of diphenylketene. Grotjahn, D. B.; Bikzhanova, G. A.; Collins, L. S. B.; Concolino, T.; Lam, K.-C.; Rheingold, A. L. J. Am. Chem. Soc. 2000, 122, 5222.
30. Hofmann, P.; Meier, C.; Eglert, U.; Schmidt, M. U. Chem. Ber. 1992, 125, 353.
31. Bianchini, C.; Meli, A.; Peruzzini, M.; Vizza, F.; Frediana, P.; Ramirez, J. A. Organometallics 1990, 9, 226.
32. References for typical P-M-P angles for second- and third-row (dtbpm)M complexes: Urtel, H.; Meier, C.; Eisentraeger, F.; Rominger, F.; Joschek, J. P.; Hofmann, P. Angew. Chem., Int. Ed. 2001, 40, 781.
33. Hofmann, P.; Heiss, H.; Neiteler, P.; Mueller, G.; Lachmann, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 880.
34. Hofmann, P.; Heiss, H.; Mueller, G. Z. Naturforsch. 1987, 42b, 395.
35. (a) Edelbach, B. L.; Lachicotte, R. J.; Jones, W. D. Organometallics 1999, 18, 4040.
36. (b) Edelbach, B. L.; Lachicotte, R. J.; Jones, W. D. Organometallics 1999, 18, 4660.
37. With phenylacetylene, trace amounts (approximately 3%) of 2 + 1 (2 alkyne + biphenylene) products were observed by GC/MS analysis (m/z = 356 for parent ion).
38. The structures of compounds 9 and 10 were verified by NMR and chemical methods. In particular, separate hydrogenolysis of 9 and 10 over Pd/C yielded the identical product, 9-(1-trimethylsilylethyl)-fluorene. See Supporting Information for details of these reactions.
39. Werner, H.; Lass, R. W.; Gevert, O.; Wolf, J. Organometallics 1997, 16, 4077.
40. Werner, H.; Baum, M.; Schneider, D.; Windmueller, B. Organometallics 1994, 13, 1089.
41. Rappert, T.; Nuernberg, O.; Werner, H. Organometallics 1993, 12, 1359.
42. Compounds 9 and 10 do not interconvert by either acid or base catalysis. We also considered that a metal-containing product formed during the course of the reaction promoted an isomerization. However, when a solution of either 9 or 10 was added to the reaction mixture upon completion of a catalytic run and heated at 125 °C, no discernible change in the ratio of the compounds was observed.
43. Catellani, M.; Chiusoli, G. P. J. Organomet. Chem. 1985, 286, C13.
44. This transformation has been reported before in our labs via base-assisted palladium catalysis. Satoh, T.; Jones, W. D. Organometallics 2001, 20, 2916.
45. The true cis/trans product ratio in these reactions is unknown, as isomerization occurs under the reaction conditions, presumably via a rhodium-promoted pathway. The E isomer is always formed in a higher amount initially, however, and is slowly converted to the Z isomer.
46. Yates, P. Organic Synthesis; Wiley: New York, 1973; Collect. Vol. 5, p 772.