Mild and efficient aryl-alkenyl coupling via Pd(II) catalysis in the presence of oxygen or Cu(II) oxidants

Journal of Organic Chemistry

Volumn 67, Issue 20, 2002, Pages 7127-7130

  Parrish, Jay P ^a   Jung, Young Chun ^a   Shin, Seung Il ^a   Jung, Kyung Woon ^a  

^a UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COUPLING METHODS;

CATALYSIS; CHEMICAL BONDS; COPPER; ELECTRONS; OXIDATION; OXYGEN; PALLADIUM;

OLEFINS;

ALKENE; ALKENYL GROUP; COPPER; LEAD; OXIDIZING AGENT; OXYGEN;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; ELECTRON; METAL BINDING; OXIDATION; REACTION ANALYSIS;

ALKENES; CATALYSIS; CHEMISTRY, ORGANIC; COPPER; HYDROCARBONS, AROMATIC; MOLECULAR STRUCTURE; OXIDANTS; OXIDATION-REDUCTION; OXYGEN; PALLADIUM; STEREOISOMERISM;

EID: 0037020007     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020159p     Document Type: Article

References (55)

1. (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
2. (b) Ikeda, M.; El Bialy, S. A. A.; Yakura, T. Heterocycles 1999, 51, 1957.
3. (c) Shibasaki, M.; Boden, C. O. J.; Kojima, A. Tetrahedron 1997, 53, 7371.
4. (d) Gibson, S. E.; Middleton, R. J. Contemp. Org. Synth. 1996, 3, 447.
5. (e) Negishi, E.; Coperet, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365.
6. (f) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
7. (g) Heck, R. F. Org. React. 1982, 27, 345
8. (h) Heck, R. F. Acc. Chem. Res. 1979, 12, 146.
9. (a) Brase, S.; de Meijere, A. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley: New York, 1998; pp 99-166.
10. (b) Link, J. T.; Overman, L. E. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley: New York, 1998; pp 231-269.
11. (a) Muratake, H.; Abe, I.; Natsume, M. Tetrahedron Lett. 1994, 35, 2573.
12. (b) Kojima, A.; Takemoto, T.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1996, 61, 4876.
13. (c) Overman, L. E.; Ricca, D. J.; Tran, V. D. J. Am. Chem. Soc. 1997, 119, 12031.
14. (d) Tietze, L. F.; Schirok, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1124.
15. For recent examples of low-temperature traditional Heck reactions, see: (a) Jeffery, T. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI: London, UK, 1996; pp 153-260. For examples of low-temperature Heck reactions with aryl chlorides, see: (b) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989.
16. For recent examples of low-temperature traditional Heck reactions, see: (a) Jeffery, T. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI: London, UK, 1996; pp 153-260. For examples of low-temperature Heck reactions with aryl chlorides, see: (b) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989.
17. (a) Cho, C. S.; Motofusa, S.-I.; Ohe, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1996, 69, 2341.
18. (b) Oda, H.; Morishita, M.; Fugami, K.; Sano, H.; Kosugi, M. Chem. Lett. 1996, 811.
19. (c) Fugami, K.; Hagiwara, S.; Oda, H.; Kosugi, M. Synlett 1998, 477.
20. (d) Oi, S.; Moro, M.; Ono, S.; Inoue, Y. Chem. Lett. 1998, 83.
21. (e) Kang, S.-K.; Choi, S.-C.; Ryu, H.-C.; Yamaguchi, T. J. Org. Chem. 1998, 63, 5748.
22. (f) Matoba, K.; Motofusa, S.-I.; Cho, C. S.; Ohe, K.; Uemura, S. J. Organomet. Chem. 1999, 574, 3.
23. For the initial report, see: Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5518. For the mechanistic rationale, see: (a) Heck, R. F. J. Am. Chem. Soc. 1969, 91, 6707. (b) Heck, R. F. J. Am. Chem. Soc. 1971, 93, 6896.
24. For the initial report, see: Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5518. For the mechanistic rationale, see: (a) Heck, R. F. J. Am. Chem. Soc. 1969, 91, 6707. (b) Heck, R. F. J. Am. Chem. Soc. 1971, 93, 6896.
25. For the initial report, see: Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5518. For the mechanistic rationale, see: (a) Heck, R. F. J. Am. Chem. Soc. 1969, 91, 6707. (b) Heck, R. F. J. Am. Chem. Soc. 1971, 93, 6896.
26. (a) Hirabayashi, K.; Ando, J.-I.; Nishihara, Y.; Mori, A.; Hiyama, T. Synlett 1999, 99.
27. (b) Hirabayashi, K.; Ando, J.-I.; Kawashima, J.; Nishihara, Y.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 1409.
28. Negishi, E.; Coperet, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365.
29. 2 effected chloroalkylation to produce iii in 73% yield. We think that the desired product ii does form, but reacts quickly by recoordinating with Pd(II). After metal-olefin coordination, chloride attacks the most activated, electron poor position, which is usually benzylic in our examples.
30. For examples of chloroalkylation, see: (a) Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5538. (b) Backvell, J.-E.; Nordberg, R. E. J. Am. Chem. Soc. 1980, 102, 393. (c) Tamaru, Y.; Hojo, M.; Higashimura, H.; Yoshida, Z. Angew. Chem., Int. Ed. Engl. 1986, 25, 735.
31. For examples of chloroalkylation, see: (a) Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5538. (b) Backvell, J.-E.; Nordberg, R. E. J. Am. Chem. Soc. 1980, 102, 393. (c) Tamaru, Y.; Hojo, M.; Higashimura, H.; Yoshida, Z. Angew. Chem., Int. Ed. Engl. 1986, 25, 735.
32. For examples of chloroalkylation, see: (a) Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5538. (b) Backvell, J.-E.; Nordberg, R. E. J. Am. Chem. Soc. 1980, 102, 393. (c) Tamaru, Y.; Hojo, M.; Higashimura, H.; Yoshida, Z. Angew. Chem., Int. Ed. Engl. 1986, 25, 735.
33. The oxidation of Pd(0) is aided by the presence of chloride ions, which helps to stabilize Pd(II) and Cu. For a reference, see: Jira, R.; Freiesleben, W. Organomet. React. 1972, 3, 5.
34. (a) Smidt, J. Chem. Ind. 1962, 54.
35. (b) Smidt, J.; Hafner, W.; Jira, R.; Sieber, R.; Sedlmeier, J.; Sabel, J. Angew. Chem., Int. Ed. Engl. 1962, 1, 80.
36. (c) Smidt, J.; Hafner, W.; Jira, R.; Sedlmeier, J.; Sieber, R.; Ruttinger, R.; Kojer, H. Angew. Chem. 1959, 71, 176.
37. Tsuji, J. Palladium Reagents and Catalysis, Innovations in Organic Synthesis; Wiley: New York, 1996; pp 19- 124.
38. (a) Tsuji, J.; Shimizi, I.; Kobayashi, Y. Isr. J. Chem. 1984, 24, 153.
39. (b) Tsuji, J.; Shimizi, I.; Yamamoto, K. Tetrahedron Lett. 1976, 17, 2975.
40. (c) McOuillin, F. J.; Parker, D. G. J. Chem. Soc., Perkin Trans. 1 1974, 809.
41. (a) Wong, M. S.; Zhang, X. L. Tetrahedron Lett. 2001, 42, 4087.
42. (b) Smith, K. A.; Campi, E. M.; Jackson, W. R.; Marcuccio, S.; Naeslund, C. G. M.; Deacon, G. B. Synlett 1997, 131.
43. (c) Alcaraz, L.; Taylor, R. J. K. Synlett 1997, 791.
44. (d) Shirakawa, E.; Murota, Y.; Nakao, Y.; Hiyama, T. Synlett 1997, 1143.
45. (e) Moreno-Manas, M.; Perez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346.
46. (a) Weissman, H.; Song, X.; Milstein, D. J. Am. Chem. Soc. 2001, 123, 337.
47. (b) Matoba, K.; Motofusa, S.-I.; Cho, C. S.; Ohe, K.; Uemura, S. J. Organomet. Chem. 1999, 574, 3.
48. (c) Miura, M.; Tsuda, T.; Satoh, T.; Pivsa-Art, S.; Nomura, M. J. Org. Chem. 1998, 63, 5211.
49. (a) van Benthem, R. A. T. M.; Hiemstra, H.; Michels, J. J.; Speckamp, W. N. J. Chem. Soc., Chem. Commun. 1994, 357.
50. (b) Larock, R. C.; Hightower, T. R. J. Org. Chem. 1993, 58, 5298.
51. (a) Stahl, S. S.; Thorman, J. L.; Nelson, R. C.; Kozee, M. A. J. Am. Chem. Soc. 2001, 123, 7188.
52. (b) Thiel, W. R. Angew. Chem., Int. Ed. Engl. 1999, 38, 3157.
53. (a) Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5518.
54. For recent examples, see: (b) Hirabayashi, K.; Ando, J.-I.; Kawashima, J.; Nishihara, Y.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 1409.
55. (c) Hirabayashi, K.; Ando, J.-I.; Nishihara, Y.; Mori, A.; Hiyama, T. Synlett 1999, 99.