An anionic rhodium η4-quinonoid complex as a multifunctional catalyst for the arylation of aldehydes with arylboronic acids

Journal of the American Chemical Society

Volumn 127, Issue 35, 2005, Pages 12238-12239

  Son, Seung Uk ^b   Kim, Sang Bok ^a   Reingold, Jeffrey A ^a   Carpenter, Gene B ^a   Sweigart, Dwight A ^a  

^a BROWN UNIVERSITY   (United States)

^b Sungkyunkwan University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BORONIC ACID DERIVATIVE; QUINONE DERIVATIVE; RHODIUM;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; CRYSTAL STRUCTURE; ELECTRON TRANSPORT; PROTON TRANSPORT; REACTION ANALYSIS;

EID: 24644431886     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0537981     Document Type: Article

References (41)

1. (a) Pierpont, C. G.; Langi, C. W. Prog. Inorg. Chem. 1994, 41, 331.
2. (b) Ebadi, M.; Lever, A. B. P. Inorg. Chem. 1999, 38, 467.
3. (c) Coenzyme Q: Biochemistry, Bioenergetics and Clinical Applications of Ubiquinone; Lenaz, G., Ed.; Wiley: New York. 1985.
4. (a) Huang, Y.-S.; Sabo-Etienne, S.; He, X.-D.; Chaudret, B. Organometallics 1992, 11, 303.
5. (b) Koelle, U.; Weisschädel, C.; Englert, U. J. Organomet. Chem. 1995, 490, 101.
6. (c) Schumann, H.; Arif, A. M.; Richmond, T. G. Polyhedron 1990, 9, 1677.
7. (a) Sun, S.; Carpenter, G. B.; Sweigart, D. A. J. Organomet. Chem. 1996, 512, 257.
8. (b) Le Bras, J.; Amouri, H.; Vaissermann, J. Organometallics 1998, 17, 1116.
9. (c) Oh, M.; Carpenter, G. B.; Sweigart, D. A. Organometallics 2002, 21, 1290.
10. (d) Moussa, J.; Guyard-Duhayon, C.; Herson, P.; Amouri, H.; Rager, M. N.; Jutand, A. Organometallics 2004, 23, 6231.
11. (e) Fairhurst, G.; White, C. J. Chem. Soc., Dalton Trans. 1979, 1531.
12. See Supporting Information for details.
13. -. See: Oh, M.; Carpenter, G. B.; Sweigart, D. A. Acc. Chem. Res. 2004, 37, 1.
14. (a) Casey, C. P.; Johnson, J. B.; Singer, S. W.; Cui, Q. J. Am. Chem. Soc. 2005, 127, 3100.
15. (b) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97.
16. (c) Josephsohn, N. S.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 11594.
17. (d) Mermerian, A. H.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 4050.
18. X-ray data for this salt were (to date) of only moderate quality, but nevertheless sufficient to establish the connectivity shown.
19. (a) Suzuki, A. Acc. Chem. Res. 1982, 15, 178.
20. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
21. (a) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279.
22. (b) Ueda, M.; Miyaura, N. J. Org. Chem. 2000, 65, 4450.
23. (c) Fürstner. A.; Krause, H. Adv. Synth. Catal. 2001, 343.
24. (d) Pucheault, M.; Darses, S.; Genet, J.-P. J. Am. Chem. Soc. 2004, 126, 15356.
25. (a) Takaya, Y.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 1998, 120, 5579.
26. (b) Batey, R. A.; Thadani, A. N.; Smil, D. V. Org. Lett. 1999, 1, 1683.
27. (c) Ramnauth, J.; Poulin, O.; Bratovanov, S. S.; Rakhit, S.; Maddaford, S. P. Org. Lett. 2001, 3, 2571.
28. (d) Kuriyama, M.; Nagai, K.; Yamada, K.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932.
29. (e) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052.
30. (f) Yoshida, K.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 10984.
31. (g) Itooka, R.; Iguchi, Y.; Miyaura, N. J. Org. Chem. 2003, 68, 6000.
32. (h) Duursma, A.; Boiteau, J.-G.; Kefort, L.; Boogers, J. A. F.; de Vries, A. H. M.; de Vries, J. G.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2004, 69, 8045.
33. Sammis, G. M.; Danjo, H.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 9928.
34. (a) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187.
35. (b) Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 16178.
36. (c) Li, C.; Eidjaja, E.; Garland, M. J. Am. Chem. Soc. 2003, 125, 5540.
37. (d) Guo, N.; Li, L.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 6542.
38. (e) Comte, V.; Le Gendre, P.; Richard, P.; Moïse, C. Organometallics 2005, 24, 1439.
39. Braga, A. A. C.; Morgon, N. H.; Ujaque, G.; Maseras, F. J. Am. Chem. Soc. 2005, 127, ASAP.
40. - present indicate that an interaction occurs.
41. 9a.b