Carbon-carbon coupling of C(sp3)-F bonds using alumenium catalysis

Journal of the American Chemical Society

Volumn 131, Issue 31, 2009, Pages 11203-11212

  Gu, Weixing ^a,b   Haneline, Mason R ^b,c   Douvris, Christos ^b,d   Ozerov, Oleg V ^a,b  

^a TEXAS A AND M UNIVERSITY   (United States)

^b BRANDEIS UNIVERSITY   (United States)

^c Heraeus Metal Processing Inc   (United States)

^d UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUPS; ALKYL SUBSTITUENT; ALKYLALUMINUM; C-F ACTIVATION; C-F BONDS; CARBON-CARBON COUPLING; DEFLUORINATION; HIGH FIDELITY; METHYLALUMINOXANE; ORGANOALUMINUM COMPOUNDS; REACTION MIXTURE; REACTIVE SUBSTRATES; STOICHIOMETRIC REAGENTS; TRIALKYLALUMINUM;

ALUMINUM; ALUMINUM COMPOUNDS; CATALYSIS; HYDROCARBONS;

ALKYLATION;

ALKANE DERIVATIVE; ALUMINUM DERIVATIVE; ANION; CARBON; CATION; FLUORINE; SOLVENT; WATER;

ALKYLATION; ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; DEFLUORINATION; STOICHIOMETRY; TRANSPORT KINETICS;

EID: 68249141234     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja903927c     Document Type: Article

References (44)

1. (a) Hudlicky, M. Chemistry of Organic Fluorine Compounds; Prentice-Hall: New York, 1992; p 175.
2. (b) Hiyama, T. Organofluorine Compounds Chemistry and Applications; Springer: New York, 2000.
3. (a) Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 94, 373.
4. (b) Burdeniuc, J.; Jedlicka, B.; Crabtree, R. H. Chem. Ber. 1997, 130, 145.
5. (c) Richmond, T. G. In Topics in Organometallic Chemistry; Murai, S., Ed.; Springer: New York, 1999; Vol. 3, p 243.
6. (d) Reinhold, M.; McGrady, J. E.; Perutz, R. N. J. Am. Chem. Soc. 2004, 126, 5268, and references within.
7. (e) Torrens, H. Coord. Chem. Rev. 2005, 249, 1957.
8. (f) Amii, H.; Uneyama, K. Chem. Rev. 2009, 109, 2119.
9. (a) Shine, K. P.; Sturges, W. T. Science 2007, 315, 1804.
10. (b) Burdeniuc, J.; Crabtree, R. H. Science 1996, 271, 340.
11. 3)-F to C-C conversion, see: (a) Terao, J.; Ikumi, A.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2003, 125, 5646.
12. (b) Terao, J.; Todo, H.; Watanabe, H.; Ikumi, A.; Kambe, N. Angew. Chem., Int. Ed. 2004, 42, 3412.
13. (c) Terao, J.; Watabe, H.; Kambe, N. J. Am. Chem. Soc. 2005, 127, 3656.
14. (d) Hatakeyama, T.; Ito, S.; Nakamura, M.; Nakamura, E. J. Am. Chem. Soc. 2005, 127, 14192.
15. (e) Fuchibe, K.; Akiyama, T. J. Am. Chem. Soc. 2006, 128, 1434.
16. (f) Fuchibe, K.; Mitomi, K.; Suzuki, R.; Akiyama, T. Chem. - Asian J. 2008, 3, 261.
17. Scott, V. J.; Çelenligil-Çetin, R.; Ozerov, O. V. J. Am. Chem. Soc. 2005, 127, 2852.
18. Panisch, R.; Bolte, M.; Mueller, T. J. Am. Chem. Soc. 2006, 128, 9676.
19. Douvris, C.; Stoyanov, E. S.; Tham, F. S.; Reed, C. A. Chem. Commun. 2007, 1145.
20. Douvris, C.; Ozerov, O. V. Science 2008, 328, 1188.
21. Krause, J. R.; Lampe, F. W. J. Phys. Chem. 1977, 81, 281.
22. (a) Kim, K.-C.; Reed, C. A.; Elliott, D. W.; Mueller, L. J.; Tham, F.; Lin, L.; Lambert, J. B. Science 2002, 297, 825.
23. (b) Reed, C. A. Acc. Chem. Res. 1998, 31, 325.
24. (c) Lambert, J. B.; Kania, L.; Zhang, S. Chem. Rev. 1995, 95, 1191.
25. (d) Reed, C. A.; Xie, Z.; Bau, R.; Benesi, A. Science 1993, 262, 402.
26. (e) Lambert, J. B.; Zhang, S. J. Chem. Soc., Chem. Commun. 1993, 383.
27. (a) Korbe, S.; Schreiber, P. J.; Michl, J. Chem. Rev. 2006, 106, 5208.
28. (b) Reed, C. A. Chem. Commun. 2005, 1669.
29. (c) Reed, C. A. Acc. Chem. Res. 1998, 31, 133.
30. (a) Fuchibe, K.; Akiyama, T. J. Am. Chem. Soc. 2006, 128, 1434.
31. (b) Fuchibe, K.; Mitomi, K.; Suzuki, R.; Akiyama, T. Chem. - Asian J. 2008, 3, 261.
32. Terao, J.; Begum, S. A.; Shinohara, Y.; Tomita, M.; Naitoh, Y.; Kambe, N. Chem. Commun. 2007, 855.
33. Klahn, M.; Fischer, C.; Spannenberg, A.; Rosenthal, U.; Krossing, I. Tetrahedron Lett. 2007, 48, 8900.
34. Kim, K. C.; Reed, C. A.; Long, G. S.; Sen, A. J. Am. Chem. Soc. 2002, 124, 7662.
35. (a) Gundersen, G.; Haugen, T.; Haaland, A. J. Organomet. Chem. 1973, 54, 77.
36. (b) Laubengayer, A. W.; Lengnick, G. F. Inorg. Chem. 1966, 5, 5037.
37. +.
38. Commercial MAO, however, has a higher than unity ratio of methyl groups to oxygens.
39. (a) Zurek, E.; Ziegler, T. Prog. Polym. Sci. 2004, 29, 107.
40. (b) Chen, E. Y. X.; Marks, T. J. Chem. Rev. 2000, 100, 1391.
41. Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255.
42. Strobach, D. R.; Boswell, G. A. J. Org. Chem. 1971, 36, 818.
43. Xie, Z. W.; Jelinek, T.; Bau, R.; Reed, C. A. J. Am. Chem. Soc. 1994, 116, 1907.
44. Xie, Z. W.; Manning, J.; Reed, R. W.; Mathur, R.; Boyd, P. D. W.; Benesi, A.; Reed, C. A. J. Am. Chem. Soc. 1996, 118, 2922.