Addition and coupling reactions of bis(pinacolato)diboron mediated by CuCl in the presence of potassium acetate

Chemistry Letters

Volumn , Issue 9, 2000, Pages 982-983

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

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034339877     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.982     Document Type: Article

References (20)

1. T. Ishiyama and N. Miyaura, Journal of Synthetic Organic Chemistry, 57, 503 (1999).
2. T. Ishiyama, M. Yamamoto, N. Miyaura, Chem. Commun., 1997, 689; C. N. Iverson, M.R. Smith III, Organometallics, 16, 2757 (1997).
3. T. Ishiyama, M. Yamamoto, N. Miyaura, Chem. Commun., 1997, 689; C. N. Iverson, M.R. Smith III, Organometallics, 16, 2757 (1997).
4. T. Ishiyama, N. Matsuda, N. Miyaura, A. Suzuki, J. Am. Chem. Soc., 115, 11018 (1993); T. Ishiyama, N. Matsuda, M. Murata, F. Ozawa, A. Suzuki, N. Miyaura, Organometallics, 15, 713 (1996); C. N. Iverson, M. R. Smith III, Organometallics, 15, 5155 (1996); G. Lesley, P. Nguyen, N. J. Taylor, T. B. Marder, A. J. Scott, W. Clegg, N. C. Norman, Organometallics, 15, 5137 (1996).
5. T. Ishiyama, N. Matsuda, N. Miyaura, A. Suzuki, J. Am. Chem. Soc., 115, 11018 (1993); T. Ishiyama, N. Matsuda, M. Murata, F. Ozawa, A. Suzuki, N. Miyaura, Organometallics, 15, 713 (1996); C. N. Iverson, M. R. Smith III, Organometallics, 15, 5155 (1996); G. Lesley, P. Nguyen, N. J. Taylor, T. B. Marder, A. J. Scott, W. Clegg, N. C. Norman, Organometallics, 15, 5137 (1996).
6. T. Ishiyama, N. Matsuda, N. Miyaura, A. Suzuki, J. Am. Chem. Soc., 115, 11018 (1993); T. Ishiyama, N. Matsuda, M. Murata, F. Ozawa, A. Suzuki, N. Miyaura, Organometallics, 15, 713 (1996); C. N. Iverson, M. R. Smith III, Organometallics, 15, 5155 (1996); G. Lesley, P. Nguyen, N. J. Taylor, T. B. Marder, A. J. Scott, W. Clegg, N. C. Norman, Organometallics, 15, 5137 (1996).
7. T. Ishiyama, N. Matsuda, N. Miyaura, A. Suzuki, J. Am. Chem. Soc., 115, 11018 (1993); T. Ishiyama, N. Matsuda, M. Murata, F. Ozawa, A. Suzuki, N. Miyaura, Organometallics, 15, 713 (1996); C. N. Iverson, M. R. Smith III, Organometallics, 15, 5155 (1996); G. Lesley, P. Nguyen, N. J. Taylor, T. B. Marder, A. J. Scott, W. Clegg, N. C. Norman, Organometallics, 15, 5137 (1996).
8. T. Ishiyama, M. Yamamoto, N. Miyaura, Chem. Commun., 1996, 2073.
9. T. D. Parsons, E. D. Baker, A. B. Burg, and G. L. Juvinall, J. Am. Chem. Soc., 83, 250 (1961); T. D. Parsons, J. M. Self, and L. H. Schaad, J. Am. Chem. Soc., 89, 3446 (1967); G. Schmid and H. Nöth, Chem. Ber., 101, 2502 (1968).
10. T. D. Parsons, E. D. Baker, A. B. Burg, and G. L. Juvinall, J. Am. Chem. Soc., 83, 250 (1961); T. D. Parsons, J. M. Self, and L. H. Schaad, J. Am. Chem. Soc., 89, 3446 (1967); G. Schmid and H. Nöth, Chem. Ber., 101, 2502 (1968).
11. T. D. Parsons, E. D. Baker, A. B. Burg, and G. L. Juvinall, J. Am. Chem. Soc., 83, 250 (1961); T. D. Parsons, J. M. Self, and L. H. Schaad, J. Am. Chem. Soc., 89, 3446 (1967); G. Schmid and H. Nöth, Chem. Ber., 101, 2502 (1968).
12. During the course of our study, the copper-catalyzed addition of diboron 1 to enones was reported. We thank Professor Akira Hosomi for sending a manuscript prior to publication; H. Ito, H. Yamanaka, and A. Hosomi, 78th Annual Meeting of Chemical Society of Japan, March 2000, IF534. Tetrahedron Lett., in press.
13. B. H. Lipshultz, in "Organometallics in Synthesis," ed. by M. Schlosser, Wiley, Chichester (1994), pp. 283-382.
14. J. F. Normant, Pure Appl. Chem., 50, 709 (1978).
15. I. Fleming, T. W. Newton, F. Roessler, J. Chem. Soc., Perkin Trans. 1, 1981, 2527.
16. E. Piers and J. M. Chong, Can. J. Chem., 66, 1425 (1988); B. M. Lipshutz, S. Sharma, and D. C. Reuter, Tetrahedron Lett., 31, 7253 (1990).
17. E. Piers and J. M. Chong, Can. J. Chem., 66, 1425 (1988); B. M. Lipshutz, S. Sharma, and D. C. Reuter, Tetrahedron Lett., 31, 7253 (1990).
18. N. Miyaura, M. Ito, and A. Suzuki, Tetrahedron Lett., 1976, 255; N. Miyaura, M. Ito, and A. Suzuki, Synthesis, 1976, 618.
19. N. Miyaura, M. Ito, and A. Suzuki, Tetrahedron Lett., 1976, 255; N. Miyaura, M. Ito, and A. Suzuki, Synthesis, 1976, 618.
20. T. Ishiyama, T. Hayashi, and N. Miyaura, unpublished results.