Palladium-catalyzed hydrophenylation of alkynes with sodium tetraphenylborate under mild conditions

Journal of Organic Chemistry

Volumn 73, Issue 2, 2008, Pages 558-562

  Zeng, Hanxiang ^a   Hua, Ruimao ^a  

^a Tsinghua University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; CATALYST ACTIVITY; OLEFINS; PALLADIUM;

MILD CONDITIONS; SODIUM TETRAPHENYLBORATE;

SODIUM CHLORIDE;

ACETIC ACID; ALKYNE DERIVATIVE; LEAD CHLORIDE; PALLADIUM; TETRAPHENYLBORON; ALKENE; ALKYNE; ORGANOMETALLIC COMPOUND;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKENES; ALKYNES; CATALYSIS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; STEREOISOMERISM; TETRAPHENYLBORATE;

EID: 40949143965     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7020554     Document Type: Article

References (32)

1. Selected examples: (a) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992-1995.
2. (b) Lim, Y.-G.; Lee, K.-H.; Koo, B. T.; Kang, J.-B. Tetrahedron Lett. 2001, 42, 7609-7612.
3. (c) Tsukada, N.; Mitsuboshi, T.; Setoguchi, H.; Inoue, Y. J. Am. Chem. Soc. 2003, 125, 12102-12103.
4. (d) Karshtedt, D.; Bell, A. T.; Tilley, T. D. Organometallics 2004, 23, 4169-4171.
5. Selected examples: (a) Yamaguchi, M.; Kido, Y.; Hayashi, A.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1313-1315.
6. (b) Yonehara, F.; Kido, Y.; Yamaguchi, M. Chem. Commun. 2000, 1189-1190.
7. (c) Reetz, M. T.; Sommer, K. Eur. J. Org. Chem. 2003, 3485-3496.
8. Matoba, K.; Motofusa, S.-i.; Cho, C. S.; Ohe, K.; Uemura, S. J. Organomet. Chem. 1999, 574, 3-10.
9. Ohe, T.; Uemura, S. Tetrahedron Lett. 2002, 43, 1269-1271.
10. Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229-4231.
11. Selected examples: (a) Takaya, Y.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 1998, 120, 5579-5580.
12. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1999, 40, 6957-6961.
13. (c) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999, 121, 11591-11592.
14. (d) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852-6856.
15. (e) Hayashi, T.; Ueyama, K.; Tokunaga, N.; Yoshida, K. J. Am. Chem. Soc. 2003, 125, 11508-11509.
16. (f) Otomaru, Y.; Kina, A.; Shintani, R.; Hayashi, T. Tetrahedron: Asymmetry 2005, 16, 1673-1679.
17. (g) Chen, F.-X.; Kina, A.; Hayashi, T. Org. Lett. 2006, 8, 341-344.
18. (a) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918-9919.
19. (b) Shirakawa, E.; Takahashi, G.; Tsuchimoto, T.; Kawakami, Y. Chem. Commun. 2001, 2688-2689.
20. (a) Shintani, R.; Okamoto, K.; Otomaru, Y.; Ueyama, K.; Hayashi, T. J. Am. Chem. Soc. 2004, 127, 54-55.
21. (b) Shintani, R.; Tsurusaki, A.; Okamoto, K.; Hayashi, T. Angew. Chem., Int. Ed. 2005, 44, 3909-3912.
22. (a) Cho, C. S.; Uemura, S. J. Organomet. Chem. 1994, 465, 85-92.
23. (b) Cho, C. S.; Motofusa, S.-i.; Ohe, K.; Uemura, S. J. Org. Chem. 1995, 60, 883-888.
24. Wang, J.-X.; Yang, Y.; Wei, B. Synth. Commun. 2004, 34, 2063-2069.
25. Oxidative addition of a carbon-boron bond to Pd(0) has so far been proposed in several cases: (a) Ohe, T.; Ohe, K.; Uemura, S.; Sugita, N. J. Organomet. Chem. 1988, 344, C5.
26. (b) Cho, C. S.; Uemura, S. J. Organomet. Chem. 1994, 465, 85-92.
27. (c) Cho, C. S.; Motofusa, S.-i.; Ohe, K.; Uemura, S. J. Org. Chem. 1995, 60, 883-888.
28. The interaction of carbonyl group and transition metal complex has been previously reported in catalyzed 1,4-additions. See refs 5 and 8.
29. For review, see: Lappert, M. F. Chem. Rev. 1956, 56, 959-1064.
30. Tian, Q.; Larock, C. L. Org. Lett. 2000, 2, 3329-3332.
31. Yoshida, K.; Hayashi, T. J. Am. Chem. Soc. 2003, 125, 2872-2873.
32. Song, C. E.; Jung, D.-u.; Choung, S. Y.; Roh, E. J.; Lee, S.-g.; Angew. Chem., Int. Ed. 2004, 43, 6183-6185.