Synthesis of tetrasubstituted olefins by Pd-catalyzed addition of arylboronic acids to internal alkynes

Organic Letters

Volumn 7, Issue 2, 2005, Pages 259-262

  Zhou, Chengxiang ^a   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; BORONIC ACID DERIVATIVE; ESTER DERIVATIVE; PALLADIUM COMPLEX;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 13444301240     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047759q     Document Type: Article

References (39)

1. For recent representative examples, see: (a) Itami, K.; Mineno, M.; Muraoka, N.; Yoshida, J. J. Am. Chem. Soc. 2004, 126, 11778. (b) Liu, X.; Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2004, 43, 879. (c) Zhu, N.; Hall, D. G. J. Org. Chem. 2003, 68, 6066. (d) Itami, K.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2003, 125, 14670. (e) Shindo, M.; Matsumoto, K.; Mori, S.; Shishido, K. J. Am. Chem. Soc. 2002, 124, 6840.
2. For recent representative examples, see: (a) Itami, K.; Mineno, M.; Muraoka, N.; Yoshida, J. J. Am. Chem. Soc. 2004, 126, 11778. (b) Liu, X.; Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2004, 43, 879. (c) Zhu, N.; Hall, D. G. J. Org. Chem. 2003, 68, 6066. (d) Itami, K.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2003, 125, 14670. (e) Shindo, M.; Matsumoto, K.; Mori, S.; Shishido, K. J. Am. Chem. Soc. 2002, 124, 6840.
3. For recent representative examples, see: (a) Itami, K.; Mineno, M.; Muraoka, N.; Yoshida, J. J. Am. Chem. Soc. 2004, 126, 11778. (b) Liu, X.; Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2004, 43, 879. (c) Zhu, N.; Hall, D. G. J. Org. Chem. 2003, 68, 6066. (d) Itami, K.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2003, 125, 14670. (e) Shindo, M.; Matsumoto, K.; Mori, S.; Shishido, K. J. Am. Chem. Soc. 2002, 124, 6840.
4. For recent representative examples, see: (a) Itami, K.; Mineno, M.; Muraoka, N.; Yoshida, J. J. Am. Chem. Soc. 2004, 126, 11778. (b) Liu, X.; Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2004, 43, 879. (c) Zhu, N.; Hall, D. G. J. Org. Chem. 2003, 68, 6066. (d) Itami, K.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2003, 125, 14670. (e) Shindo, M.; Matsumoto, K.; Mori, S.; Shishido, K. J. Am. Chem. Soc. 2002, 124, 6840.
5. For recent representative examples, see: (a) Itami, K.; Mineno, M.; Muraoka, N.; Yoshida, J. J. Am. Chem. Soc. 2004, 126, 11778. (b) Liu, X.; Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2004, 43, 879. (c) Zhu, N.; Hall, D. G. J. Org. Chem. 2003, 68, 6066. (d) Itami, K.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2003, 125, 14670. (e) Shindo, M.; Matsumoto, K.; Mori, S.; Shishido, K. J. Am. Chem. Soc. 2002, 124, 6840.
6. (a) Tsuji, J. Palladium Reagents and Catalysis: New Perspectives for the 21st Century; John Wiley & Sons: New York, 2004.
7. (b) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; John Wiley & Sons: New York, 2002.
8. (a) Grigg, R.; Sridharan, V. Pure Appl. Chem. 1998, 70, 1047.
9. (b) Grigg, R.; Sridharan, V. J. Organomet. Chem. 1999, 576, 65.
10. (c) Poli, G.; Giambastiani, G.; Heumann, A. Tetrahedron 2000, 56, 5959.
11. (d) Fretwell, P.; Grigg, R.; Sansano, J. M.; Sridharan, V.; Sukirthalingam, S.; Wilson, D.; Redpath, J. Tetrahedron 2000, 56, 7525.
12. (a) Zhou, C.; Emrich, D. E.; Larock, R. C. Org. Lett. 2003, 5, 1579.
13. (b) Zhang, X.; Larock, R. C. Org. Lett. 2003, 5, 2993.
14. (a) Oguma, K.; Miura, M.; Satoh, T.; Nomura, M. J. Am. Chem. Soc. 2000, 122, 10464.
15. (b) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martin-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358.
16. (c) Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918.
17. (d) Lautens, M.; Yoshida, M. Org. Lett. 2002, 4, 123.
18. Shirakawa, E.; Takahashi, G.; Tsuchimoto, T.; Kawakami, Y. Chem. Commun. 2001, 2688.
19. (a) Satoh, T.; Ogino, S.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. 2004, 43, 5063.
20. (b) Oh, C.; Jung H.; Kim, K.; Kim, N. Angew. Chem., Int. Ed. 2003, 42, 805.
21. (c) Oh, C.; Ryu, J. Bull. Korean Chem. Soc: 2003, 24, 1563.
22. For an example involving the formation of a highly substituted cyclopentadiene, see: (d) Du, X.; Suguro, M.; Hirabayashi, K.; Mori A. Org. Lett. 2001, 3, 3313.
23. (a) Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400 and references therein.
24. (b) Andappan, M. M. S.; Nilsson, P.; Larhed, M. Chem. Commun. 2004, 2, 218.
25. (c) Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766.
26. (d) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185.
27. (e) Larock, R. C.; Hightower, T. R. J. Org. Chem. 1993, 58, 5298.
28. For a review covering the use of molecular sieves in organic synthesis, see: De Vos, D. E.; Dams, M.; Sels, B. F.; Jacobs, P. A. Chem. Rev. 2002, 102, 3615.
29. (a) Miyaura, N.; Suzuki, A. Main Group Met. Chem. 1987, 10, 295.
30. (b) Campi, E. M.; Jackson, W. R.; Marcuccio, S. M.; Naeslund, C. G. M. J. Chem. Soc., Chem. Commun. 1994, 2393.
31. (c) Gillmann, T.; Weeber, T. Synlett 1994, 649.
32. (d) Song, Z. Z.; Wong, H. N. C. J. Org. Chem. 1994, 59, 33.
33. (e) Moreno-Manas, M.; Pérez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346.
34. (f) Wong, M. S.; Zhang, X. L. Tetrahedron Lett. 2001, 42, 4087.
35. (g) Koza, D. J.; Carita, E. Synthesis 2002, 2183.
36. (h) Falck, J. R.; Mohapatra, S.; Bondlela, M.; Venkataraman, S. K. Tetrahedron Lett. 2002, 43, 8149.
37. (i) Lei, A.; Zhang, X. Tetrahedron Lett. 2002, 43, 2525.
38. (j) Yoshida, H.; Yamaryo, Y.; Ohshita, J.; Kunai, A. Tetrahedron Lett. 2003, 44, 1541.
39. Cho, C.; Uemura, S. J. Organomet. Chem. 1994, 465, 85.