Highly efficient 1,4-additions of electron-deficient aryl boronic acids with a novel rhodium(I) quinonoid catalyst

Organometallics

Volumn 25, Issue 15, 2006, Pages 3548-3551

  Trenkle, William C ^a   Barkin, Julia L ^a   Son, Seung Uk ^a,b   Sweigart, Dwight A ^a  

^a BROWN UNIVERSITY   (United States)

^b Sungkyunkwan University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACIDS; HETEROAROMATIC COMPOUNDS; REAGENTS; RHODIUM(I) QUINONOID CATALYST;

CATALYSTS; COMPLEXATION; ELECTRONS; INORGANIC ACIDS; ORGANOMETALLICS;

RHODIUM COMPOUNDS;

EID: 33746366801     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0602557     Document Type: Article

References (23)

1. (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229-4231.
2. (b) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169-196, and references therein
3. (c) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 703, 2829-2844.
4. (d) Hayashi, T. Pure Appl. Chem. 2004, 76, 465-475.
5. (a) Schlosser, M. Organometallics in Synthesis, 2nd ed.; Wiley: New York, 2002; pp 665-816.
6. (b) Krause, N. Angew. Chem., Int. Ed. 1998, 37, 283-285, and references therein.
7. (a) Paquin, J.; Defieber, C.; Stephenson, C.; Carreira, E. M. J. Am. Chem. Soc. 2005, 727, 10850-10851.
8. (b) Ma, Y.; Song, C.; Ma, C.; Sun, Z.; Chai, Q.; Andrus, M. Angew. Chem., Int. Ed. 2003, 42, 5871-5874.
9. (c) Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 3364-3366, and references therein.
10. Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579-5580.
11. Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852-6856.
12. (a) Chapman, C. J.; Frost, C. G. Adv. Synth. Catal. 2002, 345, 353-355.
13. (b) Moss, R. J.; Wadsworth, K. J.; Chapman, C. J.; Frost, C. G. Chem. Commun. 2004, 1984-1985.
14. (c) Paquin, J.; Defieber, C.; Stephenson, C. R. J.; Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 10850-10851.
15. Son, S. U.; Kim, S. B.; Reingold, J. A.; Carpenter, G. B.; Sweigart, D. A. J. Am. Chem. Soc. 2005. 127, 12238-12239.
16. (a) Itooka, R.; Iguchi, Y.; Miyaura, N. J. Org. Chem. 2003, 68, 6000-6004. For base studies with the Suzuki coupling:
17. (b) Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972-980.
18. It was found that diethyl ether and THF can be used in place of DME; however no reaction is observed in toluene.
19. Lautens, M.; Mancuso, J.; Grover, H. Synthesis 2004, 12, 2006-2014.
20. We cannot eliminate the possibility that the lithium counterion acts as a Lewis acid to bring a boron-ate complex into proximity of the Rh center to facilitate transmetalation.
21. For mechanistic analysis with a related system: Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. them Soc. 2002, 124, 5052-5058.
22. (a) Zou, G.; Wang, Z.; Zhu, J.; Tang, J. Chem Commun. 2003, 2438-2439.
23. (b) Mon, A.; Danda, Y.; Fujii, T.; Hirabayashi, K.; Osakada, K. J. Am. Chem. Soc. 2001, 123, 10774-10775.