Microwave-enhanced palladium-catalyzed cross-coupling reactions of potassium vinyltrifluoroborates and allyl acetates: A new route to 1,4-pentadienes

Organic Letters

Volumn 8, Issue 1, 2006, Pages 11-13

  Kabalka, George W ^a   Al Masum, Mohammad ^b  

^a UNIVERSITY OF TENNESSEE   (United States)

^b TENNESSEE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 30944447695     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051955v     Document Type: Article

References (46)

1. (a) Molander, G. A.; Felix, L. A. J. Org. Chem. 2005, 70, 3950.
2. (b) De, S.; Welker, M. E. Org. Lett. 2005, 7, 2481.
3. (c) Duursma, A.; Boiteau, J.-G.; Lefort, L.; Boogers, J. A. F.; DeVries, A. H. M.; DeVries, J. G.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2004, 69, 8045.
4. (d) Fang, G.-H.; Yan, Z.-J.; Deng, M.-Z. Org. Lett. 2004, 6, 357.
5. (e) Pucheault, M.; Darses, S.; Genet, J.-P. J. Am. Chem. Soc. 2004, 126, 15356.
6. (f) Pucheault, M.; Darses, S.; Genet, J.-P. Tetrahedron Lett. 2002, 43, 6155.
7. (a) Kabalka, G. W.; Dong, G.; Venkataiah, B. Org. Lett. 2003, 5, 3803.
8. (b) Molander, G. A.; Bernardi, C. R. J. Org. Chem. 2002, 67, 8424.
9. (c) Darses, S.; Michaud, G.; Genet, J.-P. Eur. J. Org. Chem. 1999, 1875.
10. (a) Singh, R.; Viciu, M. S.; Kramareva, N.; Navarro, O.; Nolan, S. P. Org. Lett. 2005, 7, 1829.
11. (b) Alonso, D. A.; Najera, C.; Pacheco, M. C. J. Org. Chem. 2002, 67, 5588.
12. (c) Varma, R. S.; Naicker, K. P. Green Chem. 1999, 2, 247.
13. (d) Moreno-Manas, M.; Pajuelo, F.; Pleixats, R. J. Org. Chem. 1995, 60, 2396.
14. (e) Miyaura, N.; Suginome, H.; Suzuki, A. Tetrahedron Lett. 1984, 25, 761.
15. (a) Ortar, G. Tetrahedron Lett. 2003, 44, 4311.
16. (b) Bouyssi, D.; Gerusz, V.; Balme, G. Eur. J. Org. Chem. 2002, 2445.
17. (c) Legros, J.-Y.; Fiaud, J.-C. Tetrahedron Lett. 1990, 31, 7453.
18. (d) Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972.
19. (e) Miyaura, N.; Tanabe, Y.; Suginome, H.; Suzuki, A. J. Organomet. Chem. 1982, 233, C13,
20. 4 and a 10% excess of 1-hexenyl-1,3,2-benzodioxaborole. A 12% yield of the corresponding 1-phenyl-1,4-nonadiene was reported: Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972.
21. An additional example was recently reported: Kayaki, Y.; Koda, T.; Ikariya, T. Eur. J. Org. Chem. 2004, 4989.
22. (a) Durand, S.; Parrain, J.-L.; Santelli, M. J. Chem. Soc., Perkin Trans. 1 2000, 253.
23. (b) Andrey, O.; Glanzmann, C.; Landais, Y.; Parra-Rapado, L. Tetrahedron 1997, 53, 2835.
24. (c) Nicolaou, K. C.; Ramphal, J. Y.; Petasis, N. A.; Serhan, C. N. Angew. Chem., Int. Ed. Engl. 1991, 30, 1100.
25. (a) Basavaiah, D.; Sharada, D. S.; Kumaragurubaran, N.; Reddy, R. M. J. Org. Chem. 2002, 67, 7135.
26. (b) Tsukada, N.; Sato, T.; Inoue; Y. Chem. Commun. 2001, 237.
27. (c) Klaps, E.; Schmid, W. J. Org. Chem. 1999, 64, 4, 7537.
28. (d) Hara, R.; Nishihara, Y.; Landre, P. D.; Takahashi, T. Tetrahedron Lett. 1997, 38, 447.
29. (e) Prasad, A. S. B.; Knochel, P. Tetrahedron 1997, 53, 16711.
30. (f) Denmark, S. E.; Guagnano, V.; Dixon, J. A. J. Org. Chem. 1997, 62, 4610.
31. (g) Matsuhashi, H.; Hatanaka, Y.; Kuroboshi, M.; Hiyama, T. Tetrahedron Lett. 1995, 36, 1539.
32. (h) Kobayashi, Y.; Ikeda, E. Chem. Commun. 1994, 1789.
33. (i) Matsushita, H.; Negishi, E. J. Am. Chem. Soc. 1981, 103, 2882.
34. (a) Roulet, J.-M.; Deguin, B.; Vogel, P. J. Am. Chem. Soc. 1994, 116, 3639.
35. (b) Rogic, M.; Masilamani, D. J. Am. Chem. Soc. 1977, 99, 5219.
36. (a) Arvela, R. K.; Leadbeater, N. E.; Collins, M. J., Jr. Tetrahedron 2005, 61, 9349.
37. (b) Kabalka, G. W.; Al-Masum, M. Tetrahedron Lett. 2005, 46, 6329.
38. (c) Arvela, R. K.; Leadbeater, N. E. Org. Lett. 2005, 7, 2101.
39. (d) Miao, G.; Ye, P.; Yu, L.; Baldino, C. M. J. Org. Chem. 2005, 70, 2332.
40. (e) Bedford, R. B.; Butts, C. P.; Hurst, T. E.; Lidstroem, P. Adv. Synth. Catal. 2004, 346, 1627.
41. (f) Melucci, M.; Barbarella, G.; Zambianchi, M.; Di Pietro, P.; Bongini, A. J. Org. Chem. 2004, 69, 4821.
42. (g) Zhang, W.; Chen, C. H-T.; Lu, Y.; Nagashima, T. Org. Lett. 2004, 6, 1473.
43. (h) Bai, L.; Wang, J.-X.; Zhang, Y. Green Chem. 2003, 5, 615.
44. (i) Larhed, M.; Lindeberg, G.; Hallberg, A. Tetrahedron Lett. 1996, 37, 8219.
45. Vedejs, E.; Chapman, R. W.; Fields, S. C.; Lin, S.; Schrimpf, M. R. J. Org. Chem. 1995, 60, 3020.
46. 2 (0.01 mmol, 9.0 mg) and was flushed with argon. The allylating agent (0.50 mmol) and Hünig's base (1.5 mmol, 265 μL) were then added, followed by argonpurged 2-propanol/water (2:1, 5.0 mL). The resulting mixture was placed in a CEM microwave unit and allowed to react at 80°C for 10 min. The reaction mixture was then transferred to a separatory funnel and diluted with ethyl ether (2 x 15 mL) and water (15 mL). After extraction, the organic phase was separated and dried over anhydrous sodium sulfate. The ether solution was filtered and concentrated, and the product was subjected to silica gel chromatography using hexane/ethyl acetate (100/1) as eluent.