Anti-Markovnikov olefin arylation catalyzed by an iridium complex [15]

Journal of the American Chemical Society

Volumn 122, Issue 30, 2000, Pages 7414-7415

  Matsumoto, Takaya ^a   Taube, Douglas J ^b   Periana, Roy A ^b   Taube, Henry ^b   Yoshida, Hajime ^a  

^a Nippon Mitsubishi Oil Corporation   (Japan)

^b NZ Legacy LLC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; IRIDIUM; METAL COMPLEX;

ALKYLATION; CATALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; LETTER;

EID: 0034596327     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0009830     Document Type: Letter

References (33)

1. (a) Zhou, R.; Wang, C.; Hu, Y.; Flood, T. C. Organometallics 1997, 16, 434.
2. (b) Selmeczy, A. D.; Jones, W. D.; Osman, R.; Perutz, R. N. Organometallics 1995, 14, 5677.
3. (c) Meyer, T. Y.; Woerpel, K. A.; Novak, B. M.; Bergman, R. G. J. Am. Chem. Soc. 1994, 116, 10290.
4. (d) Jones, W. D.; Hessell, E. T. J. J. Am. Chem. Soc. 1992, 114, 6087.
5. (e) Boese, W. T.; Goldman, A. S. Organometallics, 1991, 10, 782-786.
6. (f) Flood, T. C. In Electron Deficient Boron Carbon Clusters; Olah, G. A., Wade, K., William, R. E., Eds.; Wiley: New York, 1991, pp 309-349.
7. (g) Kozhevnikov, I. V.; Kim, V. I.; Talzi, E. P.; Sidelnikov, V. N. J. Chem. Soc., Chem. Commun. 1985, 1392.
8. (h) Helden, R. V.; Verberg, G. Rec. Trav. Chim. 1965, 84, 1263.
9. (i) Gretz, E.; Oliver, T. F.; Sen, A. J. Am. Chem. Soc. 1987, 109, 8109.
10. (j) Hong, P.; Yamazaki, H. J. Mol. Catal. 1984, 26, 297.
11. (k) Crabtree, R. H. Chem. Rev. 1985, 85, 245.
12. (a) Fujiwara, Y.; Moritani, I.; Danno, S.; Asano, R.; Teranishi, S. J. Am. Chem. Soc. 1969, 91, 7166.
13. (b) Taraban'ko, V. E.; Kozhevnikov, I. V.; Matveev, K. I. Kinet. Katal. 1978, 19, 1160.
14. (c) Heck, R. F. In Organic Reactions; Adams, R. J., Eds.; Wiley: New York, 1982, pp 345-390.
15. (a) Iataaki, H.; Yoshimoto, H. J. Org. Chem. 1973, 38, 76.
16. (b) Rudenkov, A. I.; Mennenga, G. U.; Rachkovskaya, L. N.; Matveev, K. I.; Kozhevnikov, I. V. Kinet. Katal. 1977, 18, 915.
17. (a) Murai, S.; Chatani, N.; Kakiuchi, F. Pure Appl. Chem. 1997, 69, 589.
18. (b) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
19. (c) Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62.
20. (d) Trost, B. M.; Imi, K.; Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371.
21. (a) Lim, YG.; Han, J. S.; Koo, B. T.; Kang, J. B. Bull. Korean Chem. Soc. 1999, 20, 1097.
22. (b) Kakiuchi, F.; Sonoda, M.; Tsujimoto, T.; Chatani, N.; Murai, S. Chem. Lett. 1999, 1083.
23. Bennett, M. A.; Mitchell, T. R. B. Inorg. Chem. 1976, 15, 2936.
24. Burgoyne, E. E. A Short Course in Organic Chemistry; McGraw-Hill Book Co.: Singapore, 1985; pp 137-139.
25. Cao, Y.; Kessas, R.; Naccache, C.; Taarit, Y. B. Appl. Catal. A 1999, 184, 231.
26. In a typical reaction protocol, a 10 mL stainless autoclave, equipped with a glass insert and a magnetic stir bar is charged with 3 mL of benzene saturated with water and 1.0 mg of 1. The reactor is degassed with nitrogen, pressurized with 1.96 Mpa of ethylene and heated to 180°C with stirring for 3 h. The liquid phase was sampled and analyzed by GC (FID) and GC-MS at the end of the reaction.
27. w = 0.037, GOF = 0.74.
28. Baba, S.; Ogura, T.; Kawaguchi, S. Bull. Chem. Soc. Jpn. 1974, 47, 665.
29. Oxidative addition for the CH activation is considered along with an electrophilic substitution mechanism in light of recent reports of reaction of a cationic Ir(III) complex with CH bonds that is proposed proceed via an Ir(V) species resulting from an oxidative addition mechanism (Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 10462; Arndtsen, B. A.; Bergman, R. G. Science 1995, 270, 1970; Steven, R. K.; Tilley, D.; Bergman, R. G. J. Am. Chem. Soc. 2000, 122, 1816). Results from theoretical calculations on this reported Ir(III) system (Strout, D. L.; Zari'c, S; Niu, S.; Hall, M. B. J. Am. Chem. Soc. 1996, 118, 6068) are consistent with the proposal of an oxidative addition mechanism.
30. Oxidative addition for the CH activation is considered along with an electrophilic substitution mechanism in light of recent reports of reaction of a cationic Ir(III) complex with CH bonds that is proposed proceed via an Ir(V) species resulting from an oxidative addition mechanism (Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 10462; Arndtsen, B. A.; Bergman, R. G. Science 1995, 270, 1970; Steven, R. K.; Tilley, D.; Bergman, R. G. J. Am. Chem. Soc. 2000, 122, 1816). Results from theoretical calculations on this reported Ir(III) system (Strout, D. L.; Zari'c, S; Niu, S.; Hall, M. B. J. Am. Chem. Soc. 1996, 118, 6068) are consistent with the proposal of an oxidative addition mechanism.
31. Oxidative addition for the CH activation is considered along with an electrophilic substitution mechanism in light of recent reports of reaction of a cationic Ir(III) complex with CH bonds that is proposed proceed via an Ir(V) species resulting from an oxidative addition mechanism (Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 10462; Arndtsen, B. A.; Bergman, R. G. Science 1995, 270, 1970; Steven, R. K.; Tilley, D.; Bergman, R. G. J. Am. Chem. Soc. 2000, 122, 1816). Results from theoretical calculations on this reported Ir(III) system (Strout, D. L.; Zari'c, S; Niu, S.; Hall, M. B. J. Am. Chem. Soc. 1996, 118, 6068) are consistent with the proposal of an oxidative addition mechanism.
32. Oxidative addition for the CH activation is considered along with an electrophilic substitution mechanism in light of recent reports of reaction of a cationic Ir(III) complex with CH bonds that is proposed proceed via an Ir(V) species resulting from an oxidative addition mechanism (Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 10462; Arndtsen, B. A.; Bergman, R. G. Science 1995, 270, 1970; Steven, R. K.; Tilley, D.; Bergman, R. G. J. Am. Chem. Soc. 2000, 122, 1816). Results from theoretical calculations on this reported Ir(III) system (Strout, D. L.; Zari'c, S; Niu, S.; Hall, M. B. J. Am. Chem. Soc. 1996, 118, 6068) are consistent with the proposal of an oxidative addition mechanism.
33. Rigby, W.; Lee, H.; Bailey, P. M.; McCleverty, J. A.; Maitlis, P. M. J. Chem. Soc. Dalton 1979, 387.