Synthesis of 1-alkenylboronic esters via palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with 1-alkenyl halides and triflates

Chemistry Letters

Volumn , Issue 2, 2000, Pages 126-127

  Takahashi, Kou ^a   Takagi, Jun ^a   Ishiyama, Tatsuo ^a   Miyaura, Norio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034335972     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.126     Document Type: Article

References (18)

1. Y. Hatanaka and T. Hiyama, Tetrahedron Lett., 28, 4715 (1987); H. Matsumoto, K. Shono, and Y. Nagai, J. Organomet. Chem., 208, 145 (1981).
2. Y. Hatanaka and T. Hiyama, Tetrahedron Lett., 28, 4715 (1987); H. Matsumoto, K. Shono, and Y. Nagai, J. Organomet. Chem., 208, 145 (1981).
3. H. Azizian, C. Eaborn, and A. Pidcock, J. Organomet. Chem., 215, 49 (1981);
4. D. Azarian, S. S. Dua, C. Eaborn, and D. R. M. Walton, J. Organomet. Chem., 117, C55 (1976).
5. T. Ishiyama, M. Murata, and N. Miyaura, J. Org. Chem., 60, 7508 (1995); S. R. Piettre and S. Baltzer, Tetrahedron Lett., 38, 1197 (1997); A. Giroux, Y. Han, and P. Prasit, Tetrahedron Lett., 38, 3841 (1997).
6. T. Ishiyama, M. Murata, and N. Miyaura, J. Org. Chem., 60, 7508 (1995); S. R. Piettre and S. Baltzer, Tetrahedron Lett., 38, 1197 (1997); A. Giroux, Y. Han, and P. Prasit, Tetrahedron Lett., 38, 3841 (1997).
7. T. Ishiyama, M. Murata, and N. Miyaura, J. Org. Chem., 60, 7508 (1995); S. R. Piettre and S. Baltzer, Tetrahedron Lett., 38, 1197 (1997); A. Giroux, Y. Han, and P. Prasit, Tetrahedron Lett., 38, 3841 (1997).
8. T. Ishiyama, Y. Itoh, T. Kitano, and N. Miyaura, Tetrahedron Lett., 38, 3447 (1997).
9. T. Ishiyama, T.-a. Ahiko, and N. Miyaura, Tetrahedron Lett., 37, 6889 (1996); T.-a. Ahiko, T. Ishiyama, and N. Miyaura, Chem. Lett., 1997, 811.
10. T. Ishiyama, T.-a. Ahiko, and N. Miyaura, Tetrahedron Lett., 37, 6889 (1996); T.-a. Ahiko, T. Ishiyama, and N. Miyaura, Chem. Lett., 1997, 811.
11. M. Murata, S. Watanabe, and Y. Masuda, J. Org. Chem., 62, 6458 (1997).
12. During the course of our study, a similar cross-coupling reaction of haloalkenes with diboron 1 or pinacolborane was reported: S. M. Marcuccio, M. Rodopoulos, H. Weigold, 10th International Conference on Boron Chemistry, Durham, England, July 1999, PB-35; M. Murata, T. Oyama, S. Watanabe, and Y. Masuda, 76th Annual Meeting of Chemical Society of Japan, March 1999, 2B712.
13. During the course of our study, a similar cross-coupling reaction of haloalkenes with diboron 1 or pinacolborane was reported: S. M. Marcuccio, M. Rodopoulos, H. Weigold, 10th International Conference on Boron Chemistry, Durham, England, July 1999, PB-35; M. Murata, T. Oyama, S. Watanabe, and Y. Masuda, 76th Annual Meeting of Chemical Society of Japan, March 1999, 2B712.
14. R. F. Heck, in "Palladium Reagents in Organic Syntheses," Academic Press, New York (1985), pp. 214-242.
15. Dimers included 2-octyl-1,3-dodecadiene and 2,3-dioctyl-1,3-butadiene, but the reaction shown in entry 1 selectively gave the former diene via the head to tail coupling between 2a and 3. N. Miyaura and A. Suzuki, J. Organomet. Chem., 213, C53 (1981).
16. I. Rivera and J. A. Soderquist, Tetrahedron Lett., 32, 2311 (1991); Y. Yamamoto, R. Fujikawa, A. Yamada, and N. Miyaura, Chem. Lett., 1999, 1069.
17. I. Rivera and J. A. Soderquist, Tetrahedron Lett., 32, 2311 (1991); Y. Yamamoto, R. Fujikawa, A. Yamada, and N. Miyaura, Chem. Lett., 1999, 1069.
18. D. S. Matteson, in "Stereodirected Synthesis with Organoboranes," Springer, New York (1995), pp. 31-41.