Palladium-catalyzed hydrometalation and bismetalation of biphenylene

Organometallics

Volumn 30, Issue 15, 2011, Pages 3923-3925

  Matsuda, Takanori ^a   Kirikae, Haruki ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENYLENE; BISMETALATION; BOND METATHESIS; C-C BONDS; FOUR-MEMBERED RINGS; HYDROMETALATION; HYDROSILANES; PALLADIUM-CATALYZED REACTIONS;

CATALYSIS;

EID: 79961061005     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200436d     Document Type: Article

References (47)

1. For recent reviews, see: Jun, C.-H. Chem. Soc. Rev. 2004, 33, 610
2. Satoh, T.; Miura, M. Top. Organomet. Chem. 2005, 14, 1
3. Kondo, T.; Mitsudo, M. Chem. Lett. 2005, 34, 1462
4. Tobisu, M.; Chatani, N. Chem. Soc. Rev. 2008, 37, 300
5. Seiser, T.; Cramer, M. Org. Biomol. Chem. 2009, 7, 2835
6. Murakami, M.; Matsuda, T. Chem. Commun. 2011, 47, 1100
7. For reviews, see: Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Simhai, N.; Iverson, C. N.; Müller, C.; Satoh, T.; Jones, W. D. J. Mol. Catal. A 2002, 189, 157
8. Steffen, A.; Ward, R. M.; Jones, W. D.; Marder, T. B. Coord. Chem. Rev. 2010, 254, 1950
9. Roske, J. P.; Stille, J. P. Macromolecules 1984, 17, 1
10. Schwager, H.; Spyroudis, S.; Vollhardt, K. P. C. J. Organomet. Chem. 1990, 382, 191
11. Edelbach, B. L.; Lachicotte, R. J.; Jones, W. D. J. Am. Chem. Soc. 1998, 120, 2843
12. Perthuisot, C.; Jones, W. D. J. Am. Chem. Soc. 1994, 116, 3647
13. Edelbach, B. L.; Vicic, D. A.; Lachicotte, R. J.; Jones, W. D. Organometallics 1998, 17, 4784
14. Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Jones, W. D. Organometallics 1997, 16, 2016
15. Edelbach, B. L.; Lachicotte, R. J.; Jones, W. D. Organometallics 1999, 18, 4040
16. Iverson, C. N.; Jones, W. D. Organometallics 2001, 20, 5745
17. Schaub, T.; Radius, U. Chem. Eur. J. 2005, 11, 5024
18. Shibata, T.; Nishizawa, G.; Endo, K. Synlett 2008, 765
19. Satoh, T.; Jones, W. D. Organometallics 2001, 20, 2916
20. For other catalytic functionalization involving C-C bond cleavage, see: Masselot, D.; Charmant, P. H.; Gallgher, T. J. Am. Chem. Soc. 2006, 128, 694
21. Saito, S.; Yoshizawa, T.; Ishigami, S.; Yamasaki, R. Tetrahedron Lett. 2010, 51, 6028
22. Edelbach, B. L.; Lachicotte, R. J.; Jones, W. D. Organometallics 1999, 18, 4660
23. Crudden, C. M.; Edwards, D. Eur. J. Org. Chem. 2003, 4695
24. Trost, B. M.; Ball, Z. T. Synthesis 2005, 853
25. Guiry, P. J.; Coyne, A. G.; Carroll, A.-M. In Comprehensive Organometallic Chemistry III; Crabtree, R. H.; Mingos, D. M. P., Eds.; Elsevier: Oxford, U.K., 2007; Vol. 10, p 839.
26. Roy, A. K. Adv. Organomet. Chem. 2008, 55, 1
27. Beletskaya, I.; Moberg, C. Chem. Rev. 2006, 106, 2320
28. Suginome, M.; Matsuda, T.; Ohmura, T.; Seki, A.; Murakami, M. In Comprehensive Organometallic Chemistry III; Crabtree, R. H.; Mingos, D. M. P., Eds.; Elsevier: Oxford, U.K., 2007; Vol. 10, p 725.
29. Burks, H. E.; Morken, J. P. Chem. Commun. 2007, 4717
30. Pubill-Ulldemolins, C.; Bonet, A.; Bo, C.; Gulyás, H.; Fernández, E. Org. Biomol. Chem. 2010, 8, 2667
31. For hydrometalative C-C bond cleavage of alkenylcyclopropanes and alkylidenecyclopropanes, see: Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Beletskaya, I. P. Tetrahedron Lett. 1995, 36, 7901
32. Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676
33. Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yureva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069
34. Itazaki, M.; Nishihara, Y.; Osakada, K. J. Org. Chem. 2002, 67, 6889
35. Simaan, S.; Goldberg, A. F. G.; Rosset, S.; Marek, I. Chem. Eur. J. 2010, 16, 774
36. For bismetalative C-C bond cleavage of alkenylcyclopropanes and alkylidenecyclopropanes, see: Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790
37. Pohlmann, T.; de Meijere, A. Org. Lett. 2000, 2, 3877
38. Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015
39. Suginome, M.; Matsuda, T.; Yoshimoto, T.; Ito, Y. Organometallics 2002, 21, 1537
40. Ohmura, T.; Taniguchi, H.; Suginome, M. Org. Lett. 2009, 11, 2880
41. For theoretical studies on palladium(0)-catalyzed bismetalation, see: Hada, M.; Tanaka, Y.; Ito, M.; Murakami, M.; Amii, H.; Ito, Y.; Nakatsuji, H. J. Am. Chem. Soc. 1994, 116, 8754
42. Sakaki, S.; Ogawa, M.; Kinoshita, M. J. Phys. Chem. 1995, 99, 9933
43. Cui, Q.; Musaev, D. G.; Morokuma, K. Organometallics 1998, 17, 1383
44. Sakaki, S.; Kai, S.; Sugimoto, M. Organometallics 1999, 18, 4825
45. Abe, Y.; Kuramoto, K.; Ehara, M.; Nakatsuji, H.; Suginome, M.; Murakami, M.; Ito, Y. Organometallics 2008, 27, 1736
46. For mechanistic studies on palladium(0)-catalyzed bismetalation, see: Murakami, M.; Yoshida, T.; Kawanami, S.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 6408
47. Yoshida, H.; Tanino, K.; Ohshita, J.; Kunai, A. Angew. Chem., Int. Ed. 2004, 43, 5052